Name: 5471-63-6|1,3-Diphenylisobenzofuran|95%
Brand: Ambeed
SKU: A425113
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1
[ 5471-63-6 ]
[ 41337-62-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With oxygen In diethyl ether at -60℃; for 2h; Irradiation;
	With carbon disulfide unter Einwirkung von Sonnenlicht;
	With diethyl ether; oxygen; methylene blue at -50℃; Irradiation;

	With oxygen; 5,15,10,20-tetraphenylporphyrin In trichlorofluoromethane at -78℃; for 2h; Irradiation;
	With oxygen In methanol
	With 6C₂₄H₁₆N₂O₂6C₁₀H₄^(2-)12Pt⁽²⁺⁾12CF₃O₃S^(1-)24C₆H₁₅P In toluene Heating;
	With oxygen Reflux;

Reference： [1]Haynes, Richard K.; Peters, Jennifer M.; Wilmot, Ian D. [Australian Journal of Chemistry, 1980, vol. 33, # 12, p. 2653 - 2661]
[2]Ecary [Annales de Chimie (Cachan, France), 1948, vol. <12> 3, p. 445,462]
[3]Rio; Scholl [Journal of the Chemical Society. Chemical communications, 1975, p. 474]
[4]Adam, Waldemar; Rodriguez, Augusto [Journal of the American Chemical Society, 1980, vol. 102, # 1, p. 404 - 406]
[5]Prasanth, Chandra Sekhar; Karunakaran, Suneesh C.; Paul, Albish K.; Kussovski, Vesselin; Mantareva, Vanya; Ramaiah, Danaboyina; Selvaraj, Leslie; Angelov, Ivan; Avramov, Latchezar; Nandakumar, Krishnankutty; Subhash, Narayanan [Photochemistry and Photobiology, 2014, vol. 90, # 3, p. 628 - 640]
[6]Fudickar, Werner; Han, Jun; He, Yan-Qin; Li, Xiaopeng; Linker, Torsten; Liu, Min; Stang, Peter J.; Tang, Jian-Hong; Wang, Heng; Wang, Zhengping; Zhong, Yu-Wu [Journal of the American Chemical Society, 2020, vol. 142, # 5, p. 2601 - 2608]
[7]Chen, Yao; Cheng, Peng; Jin, Fazheng; Lin, En; Qiao, Shan; Wang, Zhifang; Xiong, Fanhao; Yan, Dong; Yang, Yi; Zhang, Zhenjie [Journal of Materials Chemistry A, 2021, vol. 9, # 48, p. 27434 - 27441]

2
[ 5471-63-6 ]
[ 1159-86-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 9-azabicyclo<3.3.1>nonane-N-oxyl; oxygen; nitric acid In acetonitrile at 20℃; for 2h; Sealed tube; stereoselective reaction;
96%	With dihydrogen peroxide In tetrahydrofuran at 30℃; for 4.66667h;
95%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 0.0833333h;

94%	With manganese(IV) oxide In dichloromethane at 20℃; for 4h;	General procedure: MnO2 (0.57 g, 7.09 mmol) was added to a stirred solution ofbenzo[c]furan 1a (0.5 g, 1.77 mmol) in CH2Cl2 (20 mL), andthe mixture was stirred at r.t until the benzo[c]furan wasconsumed (~4 h). The mixture was then filtered throughCelite and the residue was washed with CH2Cl2 (2 × 10 mL).The combined filtrate was concentrated under reducedpressure and the residue was purified by columnchromatography (silica gel; 5% EtOAc-hexane) to give abrown solid.
94%	With dihydrogen peroxide at 45℃; for 24h;
92%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere;
91%	With sodium molybdate dihydrate; dihydrogen peroxide; sodium lauryl sulfate In dichloromethane; water monomer; butan-1-ol at 25℃; for 1.5h;
88%	With pteridin-2,4,7-trione 6,8'-endoperoxide In dichloromethane for 4h; Heating; variation of the mole ratio of reactants;
88%	With pteridin-2,4,7-trione 6,8'-endoperoxide In dichloromethane for 4h; Heating;
88%	With 6-phenyl-1,3,8-trimethylpteridin-2,4,7-trione 6,8'-endoperoxide In dichloromethane Heating;
88%	With CaO₂*2H₂O₂ In methanol at 50℃; for 3h;
88%	With dihydrogen peroxide In dichloromethane at 20℃; for 3h;	3.3. General procedure for oxygenation of substrates (3a-g) with the 2b/H₂O₂ system General procedure: To a suspension of substrates (3a-g, 0.5 mmol) and 35% hydrogen peroxide (443 μL, 5 mmol) in dichloromethane (4 mL) was added PDAIS (2b) (348 mg, 1 mmol) dropwise within 1 h at room temperature. The mixture was further stirred for 2 h. After removal of the solvent, ether was added to the reaction mixture to precipitate iodopolystyrene (PS-I). The formed PS-I was recovered by washing with ether (2 x 15 mL). After the addition of 4-methoxyacetophenone as an internal standard, the organic phase was washed with water (2 x 10 mL) and brine, dried over Na2SO4 , and concentrated. The conversion of 3a-g, formation of 4a-g, and product distribution were determined directly by 1H NMR analysis of the crude mixture. Then the resulting mixture was chromatographed on a short column (silica gel, 13-15 g) using a mixture of hexane and Et2O (90:10) as an eluent to afford the desired oxygenated products.
84%	With selenium(IV) dioxide In tetrahydrofuran at 20℃; for 0.0833333h;	General procedure for oxidationof benzo[c]furans into diketonesusing SeO₂: General procedure: To astirred solution of benzo[c]furan (1.0 mmol) in dry THF (20 mL),SeO2 (1.5 mmol) was added and stirred at room temperature until the disappearance of fluorescent color of benzo[c]furan (~5-10 minutes). After that, the reaction mixture was filtered through celite bed and washed with ethyl acetate (2 x 10 mL). The combined organic layer was washed with water (2 x 30 mL) and dried (Na2SO4). Removal of solvent followed by column chromatographic purification (Silica gel, 20%EA/Hexane) afforded diketone.
82%	With 4a,8-epidioxycyclohepta[b][1,4]-dioxin-based reagent In benzene at 80℃; for 48h;
80%	With dihydrogen peroxide; Sodium hydrogenocarbonate; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 0℃;
78%	With triethylsilane; tert.-butylhydroperoxide; oxygen; cobalt(II) 2,4-pentanedionate; acetylacetone In dichloromethane; 1,2-dichloro-ethane at 40℃; for 18h; Inert atmosphere;
76%	With N-vinylbenzamide; N-methyl phenanthridinium iodide at 20℃; Irradiation;
71%	With antimonypentachloride; oxygen In dichloromethane at -78℃; for 4h; var. Lewis acids as catalysts; var. reaction conditions; other furans;
71%	With antimonypentachloride; oxygen In dichloromethane at -78℃; for 4h;
71%	With bis(acetylacetonato)nickel(II); 2,2-bis((4R,5S)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)propyl 9-oxo-9H-thioxanthene-3-carboxylate; oxygen In toluene at -15℃; for 10h; Irradiation; Inert atmosphere;
70%	With CAN In water monomer; acetonitrile for 0.5h; Ambient temperature;
70%	With phthaloylperoxide In benzene
70%	With water monomer; oxygen In 1,4-dioxane at 20℃; for 6h; Schlenk technique; Irradiation;
70%	With 1-hydroxy-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one; iron(II) phthalocyanine; bis[(2,2,2-trifluoroacetyl)oxy]palladium; trifluoroacetic acid In water monomer; dimethyl sulfoxide at 25℃; for 48h; Irradiation;
69%	With naphthalene-1-sulfonyl fluoride; lithium dipropan-2-ylazanide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Schlenk technique;	Aryne Trapping Experiments Aryne trapping experiments were performed with 1f and 6a as substratesaccording to the General Procedure (1.0 mmol scale) with LDA(1.2 mmol), 1,3-diphenylisobenzofuran (0.321 g, 1.19 mmol), andTHF (5 mL).In experiment with 1f (0.212 g, 1.01 mmol), after chromatography,1,3-diphenylisobenzofuran (0.028 g, 0.103 mmol, 9% of recovery), 1f(0.150 g, 0.712 mmol, 70% of recovery), and 1,2-dibenzoylbenzene(0.235 g, 0.821 mmol, 69% of recovery, based on 1,3-diphenylisobenzofuran)were isolated besides a mixture of ill-defined decompositionproducts (0.130 g).1,2-Dibenzoylbenzene60Isolated after trapping experiments; white solid; mp 145.5-146.5 °C;Rf = 0.24 (cyclohexane/EtOAc 6:1).1H NMR (400 MHz, CDCl3): = 7.72-7.65 (m, 4 H), 7.62-7.55 (m, 4 H),7.51-7.45 (m, 2 H), 7.37-7.30 (m, 4 H).13C NMR (100 MHz, CDCl3): = 196.4, 139.9, 137.0, 132.9, 130.3,129.7, 129.5, 128.2. In experiment with 6a (0.227 g, 1.00 mmol), after chromatography,1,3-diphenylisobenzofuran (0.138 g, 0.510 mmol, 43% of recovery)and aryne adduct 7 (0.214 g, 0.540 mmol, 54%) were isolated besidesa mixture of ill-defined decomposition products (0.109 g), which containedalso some amount of 1,2-dibenzoylbenzene.7,12-Diphenyl-7,12-dihydro-7,12-epoxybenz[a]anthracene (7)61White solid; mp 200 °C (dec.); Rf = 0.49 (cyclohexane/EtOAc 6:1).1H NMR (400 MHz, CDCl3): = 8.10-8.03 (m, 2 H), 8.03-7.98 (m, 2 H),7.85-7.80 (m, 1 H), 7.69 (ddd, J = 7.1, 1.3, 0.7 Hz, 1 H), 7.66-7.48 (m, 9H), 7.39 (ddd, J = 7.0, 1.2, 0.7 Hz, 1 H), 7.34 (ddd, J = 8.2, 6.8, 1.3 Hz, 1H), 7.26 (ddd, J = 8.3, 6.8, 1.3 Hz, 1 H), 7.05 (ddd, J = 7.6, 7.1, 1.3 Hz, 1H), 7.00 (ddd, J = 7.6, 7.1, 1.2 Hz, 1 H).13C NMR (100 MHz, CDCl3): = 153.2, 150.7, 149.3, 147.8, 134.9,134.6, 132.7, 130.2, 129.4, 128.9, 128.72, 128.70, 128.4, 128.0, 127.5,127.2, 125.9, 125.4, 125.23, 125.18, 123.6, 122.0, 120.7, 119.0, 93.0,91.0.
68%	With oxygen In tetrahydrofuran for 4h; Irradiation;
68%	With sodium lauryl sulfate In water monomer at 25℃; Irradiation;
64%	With oxygen In dichloromethane at 20℃; for 48h; Irradiation;
62%	With 1,1'-bis(diphenylphosphanyl)ferrocene; oxygen; ozone In dichloromethane at -20℃;
60%	With oxygen In tetrahydrofuran for 24h; Irradiation;
52%	With 1-methyl-3,5,6-triphenyl-2-pyrazinone 3,6-endoperoxide In toluene Heating;
41%	With 1-acetyldioxy-1-triethylsilyldioxycycloheptane; N,N,N-tributylbutan-1-aminium fluoride In tetrahydrofuran; acetonitrile at 20℃; Inert atmosphere;
	With 4-<2-(N,N-dimethylhydrazono)ethylidene>-2,6-diphenyl-4H-pyran; oxygen; rose bengal B In methanol; benzene for 0.0166667h; Irradiation; quenching of photosensitized oxygenation; quenching rate constants;
	With oxygen; benzene
1.2 g	With dihydrogen peroxide
	With dihydrogen peroxide; iron(II) ion In acetonitrile Yield given;
	With triphenyl phosphite; ozone In dichloromethane -35 deg C --> room temp.;
	Multi-step reaction with 2 steps 1: Na / tetrahydrofuran / 8 h 2: 15 percent / Methyl Iodide / 1.)-70 deg C, 2h, 2.)20 deg C, 12h
	Multi-step reaction with 2 steps 1: Na / tetrahydrofuran / 8 h
	With N-benzyl-2-pyridone 3,6-endoperoxide In chloroform-d1 at 40℃;
94 %Chromat.	With 1-acetyldioxy-1-hydroperoxy-4-tert-butylcyclohexane; anhydrous tetramethylammonium acetate; caesium fluoride In acetonitrile at 20℃; for 0.5h;
	With oxygen; [7-(dimethylamino)phenothiazin-3-ylidene]dimethylazanium chloride In methanol for 0.00138889h; Irradiation;
	With 5-(4-(4-bromobutoxyl)phenyl)10,15,20-triphenyl porphyrin In acetonitrile Photoirradiation;
	With 1-methyl-2-[2-(5,10,15,20-tetraphenylporphyrin-2-yl)vinyl]pyridinium chloride In N,N-dimethyl-formamide at 20℃; for 0.1h; Irradiation;
	Multi-step reaction with 2 steps 1: 2,4-diphenyl-1,3,2,4-diselenadiphosphetane 2,4-diselenide / dichloromethane / 4 h / 20 °C / Inert atmosphere 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
	With [Ir(dFppy)₂(phen)]PF₆; oxygen In tetrahydrofuran; dimethyl sulfoxide for 0.0277778h; Irradiation;
	With Nitrogen dioxide In 2,2,4-trimethypentane at 13℃; Inert atmosphere;
	With [Ir(methyl 4-(2-pyridyl)benzoate)(ethylenediamine)]Cl·3H2O·CH2Cl2 In dimethyl sulfoxide UV-irradiation;
	With fullerene C<SUB>60</SUB> In N,N-dimethyl-formamide Irradiation;	Photooxidation of 1,3-diphenylisobenzofuran (DPBF) Solutions of DPBF (20 μM) and fullerene in DMF were irradiated in 1 cm path length quartz cells (2 mL) with monochromatic light at λir=480 nm (fullerene absorbance 0.1). The light fluence rate was determined as 0.60 mW/cm2. The photooxidation of DPBF was studied by following the decrease of the absorbance at λmax=415 nm. After irradiation, the formation of products interfering in the absorption spectra was not detected and the absorption due to fullerene derivatives was unchanged. Thus, the absorption changes can be assigned to the photooxidation of DPBF mediated by fullerenes.
	With oxygen; C₄₆H₄₇BrN₄O₄; trifluoroacetic acid In methanol; dichloromethane at 20℃; for 0.166667h; Irradiation;
	With 6C₄₂H₃₁BF₂I₂N₆4Fe⁽²⁺⁾8C₂F₆NO₄S₂^(1-); oxygen In [D₃]acetonitrile Irradiation;
	With C₂₆H₂₂I₂N₂O₂ In aq. phosphate buffer; dimethyl sulfoxide Irradiation;	4.1.2 Evaluation of singlet oxygen generation ability General procedure: Solutions of DPBF (20 μM) and dyes (5 μM) were prepared in phosphate buffer (2 mM, pH 7.4) with 1% of DMSO. Each solution was placed in a 1 cm quartz cell and irradiated in an aerated solar box with a 250 W lamp at various time intervals. Light was filtered in an optical filter with a 515 nm cut-off.
	With amidochlorin p6 In N,N-dimethyl-formamide at 25℃; Irradiation;
	With C₁₀₂H₃₉BF₂N₂O₇ In dichloromethane Irradiation;
	With singlet oxygen In N,N-dimethyl-formamide Irradiation;
	With 4,4-difluoro-2,6-diiodo-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene; singlet oxygen In ethanol UV-irradiation;
	With C₃₄H₂₂B₂Br₂F₄N₄; oxygen In toluene at 25℃; for 0.533333h; Irradiation;	2.3 Detection of singlet oxygen by DPBF oxidation Singlet oxygen generation experiment was set up, using a 150 W xenon lamp at 0.5 mW/cm2. A toluene solution of photosensitizer (5 × 10-6 mol/L) and 1,3-diphenylisobenzofuran (6 × 10-5 mol/L) was exposed to the monochromatic light by the optical filter at the peak absorption wavelength (500 nm) for 1-2 min at 25 °C. The absorbance was measured several times after each irradiation. Reaction of 1,3-diphenylisobenzofuran with singlet oxygen was monitored by the reduction in intensity of the absorption band at 416 nm over 32 min.
	With poly-(1,3,5-tri(9H-carbazole-9-yl)benzene); air In acetonitrile Irradiation;
	With 5,10,15,20-tetrakis[4-(phenylthio)-2,3,5,6-tetrafluorophenyl]porphyrin In N,N-dimethyl-formamide Irradiation;	2.2. Singlet Oxygen Generation (¹O₂) Experiments The ability of porphyrins 3a-d to produce 1O2 was monitored using 1,3-diphenylisobenzofuran(DPBF) in aprotic solvent (DMF) [36]. The DPBF photo-oxidation method has been widely used toquantitatively analyze singlet oxygen production because the reaction product (1,2-dibenzoylbenzene)does not absorb in the visible region. In this assay, changes in DPBF absorbance are directly related tothe amount of 1O2 generated [37]. This can be observed in Figure 3, in which the first-order kinetic profile of DPBF photo-oxidation in the presence of thioaryl-porphyrin 3a was monitored at 415 nmduring irradiation with a red-light LED array system ( = 635 nm) in DMF solution. One of theimportant parameters in which to evaluate the photodynamic potential of a photosensitizer is theproduction of singlet oxygen, (FD), which is one of the most important reactive oxygen species (ROS)in photophysical and photochemical processes [38]. In this study, the singlet oxygen quantum yieldof porphyrins 3a-d was determined, and the values are presented in Table 3. As observed in Table 3,the FD found for compound 3a is close to the standard TPP and porphyrin 1 in several solvents [39-41].In the case of porphyrins 3b-d, which have S-aryl units with different substituents (b:4-CH3, c:4-Cl,d:2-NH2), the observed values are smaller than TPP (FstdD = 0.66) [38,42], although they still displayedan ability to generate singlet oxygen. This behavior could be attributed to electronic deactivationpathways of the excited state due to the presence of the substituents on the thioaryl moieties. Althoughthe ability of sulfur-porphyrin derivatives to generate 1O2 is, in general, lower than the TPP or the starting porphyrin 1, all the thioaryl derivatives, after being exposed to red light in the presence of oxygen, demonstrate potential for photodynamic therapy (PDT) applications.
	With C₄₈H₂₆N₄O₈^(4-)2Ti⁽⁴⁺⁾2O^(2-) In N,N-dimethyl-formamide Irradiation;
	With C₅₀H₃₂BBr₂F₂N₃O₂; oxygen In toluene Irradiation;
	With C₈₄H₂₉BF₂N₄; oxygen In toluene Irradiation;
	With oxygen In water monomer; acetonitrile at 25℃; Irradiation;
	With C₄₁H₃₅BBr₂F₂N₄O₂ In toluene Irradiation;
	With 2-[1-(but-2-en-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid]-5,10,15,20-tetraphenylporphyrin In N,N-dimethyl-formamide at 20℃; Irradiation;
	With singlet oxygen In N,N-dimethyl-formamide Irradiation;
	With singlet oxygen; C₁₂₉H₁₁₇Au₃N₁₂Zn_1.5 In toluene for 0.583333h; UV-irradiation;
	With C₅₁H₃₂IrN₆⁽¹⁺⁾*F₆P^(1-) In dimethyl sulfoxide Irradiation;
	With oxygen In N,N-dimethyl-formamide Irradiation;
	With singlet oxygen Irradiation;
	With oxygen In methanol Sealed tube; Irradiation;
	With oxygen
	With oxygen In toluene Irradiation;
	With magnesium(II) sulfanyl porphyrazine embedded on titanium(IV) oxide P₂₅ nanoparticles In N,N-dimethyl-formamide Irradiation;	3.5. Photocatalytic Studies The photocatalytic studies were performed using a red-light LED lamp (EcoEnergy,Gda nsk, Poland) at wavelength 665 nm, and a power adjusted to 10 mW/cm2 with theuse of an Optel radiometer. The measurements were conducted in a 10 mm quartz cuvettein N,N'-dimethylformamide (DMF). In the experiments with a reference standard1,3-diphenylisobenzofurane (DPBF), 1 mL of 0.1 mM DPBF solution in DMF was mixed with 1 mL of TiO2 dispersion in DMF (0.1 mg/mL). In the experiments with active pharmaceutical ingredients (diclofenac sodium salt and ibuprofen), DPBF was replaced by 1 mL of0.3 mM diclofenac sodium salt solution in DMF or 1 mL of 1.5 mM ibuprofen solution in DMF. The irradiations of mixtures were performed with an LED lamp within 8 min. The UV-Vis spectra were recorded every 2 min on an Ocean Optics USB 2000+ spectrometer(Ocean Optics Inc., Largo, FL, USA).
	With C₂₁H₁₉BBr₂F₂N₂; oxygen In dichloromethane; dimethyl sulfoxide Irradiation;
	With singlet oxygen; [Ru(4′-2-pyrrolyl-2,2′:6′,2″-terpyridine)(saccharinate)2(dmso)] In N,N-dimethyl-formamide at 24.84℃; UV-irradiation;
	With N,N'-bicarbazole-benzothiadiazole-based conjugated porous organic polymer In acetonitrile for 1h; Irradiation;
	With oxygen In 2-ethoxy-ethanol; N,N-dimethyl-formamide at 20℃; Irradiation;
	With [Ni(2,2'-bipyridine)₃Cl₂]; oxygen In acetonitrile at 20℃; for 0.00555556h; Inert atmosphere; Schlenk technique; Irradiation;
	With oxygen; C₃₄H₂₆IrN₆OS⁽¹⁺⁾*Cl^(1-) In acetonitrile UV-irradiation;
	With oxygen
	With N,N-dimethyl acetamide; rose bengal; lithium nitrate; oxygen Irradiation;
	With singlet oxygen; C₄₀H₂₉IrN₅OS⁽¹⁺⁾*Cl^(1-) In acetonitrile at 20℃; UV-irradiation;	2.2. Determination of the ability of ¹O₂ generation The generation of singlet oxygen (1O2) was studied for selected Ir(III) compounds in acetonitrile according to a relative procedure adapted from the literature [33-35], which is based on monitoring by UV-Vis spectroscopy the oxidation of 1,3-diphenylisobenzofuran (DPBF, yellow) to 1,2-dibenzoylbenzene (colorless) photosensitized by the Ir(III) derivatives. (0010) DPBF was selected as the 1O2 scavenger due to its fast reaction with 1O2. Air-equilibrated acetonitrile solutions containing DPBF were prepared (~8·10-5M) in a cuvette and their absorbance adjusted to around 1.0 at 410nm. Then, the complex (10-5M, corresponding to absorbance around 0.2) was introduced in the cuvette. Low dye concentrations were used to minimize quenching of 1O2 by the dyes. The mixture was irradiated with a blue LED strip (λir=460nm) at room temperature for 1s irradiation intervals during a total exposure period of 8s and absorption UV-Vis spectra were recorded after every irradiation interval.
	With singlet oxygen; C₄₀H₂₉IrN₅OS⁽¹⁺⁾*Cl^(1-) In acetonitrile at 20℃; UV-irradiation;	2.2. Determination of the ability of ¹O₂ generation The generation of singlet oxygen (1O2) was studied for selected Ir(III) compounds in acetonitrile according to a relative procedure adapted from the literature [33-35], which is based on monitoring by UV-Vis spectroscopy the oxidation of 1,3-diphenylisobenzofuran (DPBF, yellow) to 1,2-dibenzoylbenzene (colorless) photosensitized by the Ir(III) derivatives. (0010) DPBF was selected as the 1O2 scavenger due to its fast reaction with 1O2. Air-equilibrated acetonitrile solutions containing DPBF were prepared (~8·10-5M) in a cuvette and their absorbance adjusted to around 1.0 at 410nm. Then, the complex (10-5M, corresponding to absorbance around 0.2) was introduced in the cuvette. Low dye concentrations were used to minimize quenching of 1O2 by the dyes. The mixture was irradiated with a blue LED strip (λir=460nm) at room temperature for 1s irradiation intervals during a total exposure period of 8s and absorption UV-Vis spectra were recorded after every irradiation interval.

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3
[ 6903-84-0 ]
[ 5471-63-6 ]
C₂₈H₁₈N₂O₅ [ No CAS ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1989,vol. 25,p. 486 - 490
    Zhurnal Organicheskoi Khimii,1989,vol. 25,p. 542 - 547
[2]Journal of Organic Chemistry USSR (English Translation),1989,vol. 25,p. 1033 - 1039
    Zhurnal Organicheskoi Khimii,1989,vol. 25,p. 1147 - 1153
[3]Journal of Organic Chemistry USSR (English Translation),1991,vol. 27,p. 1558 - 1562
    Zhurnal Organicheskoi Khimii,1991,vol. 27,p. 1774 - 1779

4
[ 92-71-7 ]
[ 1614-12-6 ]
[ 5471-63-6 ]
[ 125282-24-8 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 929 - 935

5
[ 2274-11-5 ]
[ 5471-63-6 ]
1,8-Diphenyl-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene-9-carboxylic acid 2-acryloyloxy-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In benzene at 25℃; ΔH(excit.), ΔS(excit.);

Reference： [1]Kiselev, V. D.; Malkov, V. B.; Akhmetzyanova, G. V.; Konovalov, A. I. [Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 2.1, p. 200 - 204][Zhurnal Organicheskoi Khimii, 1990, vol. 26, # 2, p. 240 - 244]

6
[ 5471-63-6 ]
[ 23488-38-2 ]
[ 115695-55-1 ]

Reference： [1]Tetrahedron,1987,vol. 43,p. 5203 - 5224

7
[ 5471-63-6 ]
[ 3006-93-7 ]
C₃₄H₂₂N₂O₅ [ No CAS ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1989,vol. 25,p. 486 - 490
    Zhurnal Organicheskoi Khimii,1989,vol. 25,p. 542 - 547
[2]Journal of Organic Chemistry USSR (English Translation),1989,vol. 25,p. 1033 - 1039
    Zhurnal Organicheskoi Khimii,1989,vol. 25,p. 1147 - 1153
[3]Journal of Organic Chemistry USSR (English Translation),1991,vol. 27,p. 1558 - 1562
    Zhurnal Organicheskoi Khimii,1991,vol. 27,p. 1774 - 1779

8
[ 5471-63-6 ]
[ 1842-26-8 ]
[ 1499-10-1 ]
[ 134456-79-4 ]

Reference： [1]Chemische Berichte,1991,vol. 124,p. 2113 - 2118

9
[ 5471-63-6 ]
[ 1842-26-8 ]
[ 1499-10-1 ]
[ 134456-79-4 ]
[ 134456-80-7 ]
[ 1159-86-0 ]

Reference： [1]Chemische Berichte,1991,vol. 124,p. 2113 - 2118

10
[ 5471-63-6 ]
[ 22099-66-7 ]
[ 13351-26-3 ]
[ 89229-02-7 ]
[ 89229-01-6 ]
[ 89229-01-6 ]
[ 89229-01-6 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 3216 - 3218

11
[ 5471-63-6 ]
[ 13676-54-5 ]
[ 124617-66-9 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1989,vol. 25,p. 486 - 490
    Zhurnal Organicheskoi Khimii,1989,vol. 25,p. 542 - 547
[2]Journal of Organic Chemistry USSR (English Translation),1989,vol. 25,p. 1033 - 1039
    Zhurnal Organicheskoi Khimii,1989,vol. 25,p. 1147 - 1153
[3]Journal of Organic Chemistry USSR (English Translation),1991,vol. 27,p. 1558 - 1562
    Zhurnal Organicheskoi Khimii,1991,vol. 27,p. 1774 - 1779

12
[ 5471-63-6 ]
[ 129112-25-0 ]
[ 19061-38-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h;
18%	With 18-crown-6 ether; 5-(trimethylsilyl)-1,3-thiazole; cesium fluoride In tetrahydrofuran; Hexadecane; toluene at 20 - 60℃; for 23h;	6; 14 General procedure: Toluene (5 mL) was added to a mixture of cesium fluoride (0.458 g) and 18-crown-6 ether (1.571 g), and the solvent was distilled off under reduced pressure. There there are 1,3-diphenylisobenzofuran (0.406 g), 2-iodophenyltrifluoromethanesulfonic acid ester (0.350 g) and tetrahydrofuran (5 mL), 3-trimethylsilylbenzo [3,2-b] thiophene (3,2-b) 0.309 g) and hexadecane (0.227 g) as an internal standard were added, and the mixture was stirred at 60 ° C. for 21 hours. A saturated aqueous ammonium chloride solution was added to the reaction solution to stop the reaction, and the mixture was extracted with ethyl acetate. The collected organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The solvent was distilled off under reduced pressure to obtain a brown solid (1.08 g, 80%). Write the name of what the solid was in the text.

Reference： [1]Matsumoto, Takashi; Hosoya, Takamitsu; Katsuki, Miyoko; Suzuki, Keisuke [Tetrahedron Letters, 1991, vol. 32, # 46, p. 6735 - 6736]
[2]Current Patent Assignee: SAGAMI CHEMICAL RESEARCH INSTITUTE - JP2020/132537, 2020, A Location in patent: Paragraph 0056-0059

13
[ 5471-63-6 ]
[ 136639-11-7 ]
C₃₇H₃₀O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With rhodium(II) acetate In dichloromethane at 25℃; for 2h;

Reference： [1]Padwa, Albert; Austin, David J.; Gareau, Yves; Kassir, Jamal M.; Xu, Simon L. [Journal of the American Chemical Society, 1993, vol. 115, # 7, p. 2637 - 2647]

14
[ 5471-63-6 ]
[ 138091-06-2 ]
[ 138091-05-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With n-butyllithium In tetrahydrofuran at -78℃;

Reference： [1]Branan, Bruce M.; Paquette, Leo A.; Hrovat, David A.; Borden, Weston Thatcher [Journal of the American Chemical Society, 1992, vol. 114, # 2, p. 774 - 776]

15
[ 5471-63-6 ]
[ 96866-88-5 ]
[ 1499-10-1 ]

Reference： [1]Tetrahedron,1986,vol. 42,p. 1561 - 1570

16
[ 5471-63-6 ]
2-(bromomethylene)benzonorbornene [ No CAS ]
[ 13351-26-3 ]
[ 89229-02-7 ]
[ 89229-01-6 ]
[ 89229-01-6 ]
[ 89229-01-6 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 3216 - 3218

17
[ 5471-63-6 ]
2-(bromomethylene)benzonorbornene [ No CAS ]
[ 13351-26-3 ]
C₃₂H₂₄O [ No CAS ]
3,7-diphenyl-5,6;10,11-dibenzotricyclo<7.2.1.0^3,8>dodeca-5,7,10-trien-4-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 3216 - 3218

18
[ 5471-63-6 ]
2-(bromomethylene)benzonorbornene [ No CAS ]
[ 13351-26-3 ]
C₃₂H₂₄O [ No CAS ]
C₃₂H₂₄O [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 3216 - 3218

19
[ 5471-63-6 ]
3a,6a-Diiodo-octahydro-2,5-methano-pentalene [ No CAS ]
1,3-Diphenyl-isobenzofuran; compound with 1,2,3,4,5,6-hexahydro-2,5-methano-pentalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With n-butyllithium In tetrahydrofuran at -78℃;

Reference： [1]Renzoni,G.E.; Yin,T.; Borden,W.T. [Journal of the American Chemical Society, 1986, vol. 108, p. 7121]

20
[ 5471-63-6 ]
[ 208-96-8 ]
[ 36213-64-6 ]

Yield	Reaction Conditions	Operation in experiment
94.85%	In 5,5-dimethyl-1,3-cyclohexadiene Reflux;	1.1 1. In a 2000 mL three-necked flask, add 1000 mL of xylene, 1,3-diphenylisobenzofuran (100 g 370 mmol), acenaphthylene (90 g 560 mmol), and heat to reflux overnight. The solvent was evaporated under reduced pressure, and about 150 mL was remained. 500 mL of petroleum ether was added, stirred for 30 min, filtered, and the solid was vacuum dried at 60° C. for 6 h to obtain 167.5 g of a solid with a yield of 94.85%.
60%	In benzonitrile at 140℃; for 7h;

Reference： [1]Current Patent Assignee: WUHAN SHANGSAI OPTOELECTRONICS TECHNOLOGY CO LTD - CN107778199, 2018, A Location in patent: Paragraph 0058; 0064; 0070
[2]Farquhar, David; Gough, Thomas T.; Leaver, Derek; Miller, James F.; Dick, James W.; Jessep, Michael A. [Journal of the Chemical Society. Perkin transactions I, 1984, # 11, p. 2553 - 2562]

21
[ 5471-63-6 ]
[ 130-15-4 ]
[ 65869-87-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: 1,3-diphenylisobenzofuran; [1,4]naphthoquinone In dichloromethane at 20℃; for 12h; Stage #2: With boron tribromide In dichloromethane at -78℃; Reflux;
90%	Stage #1: 1,3-diphenylisobenzofuran; [1,4]naphthoquinone In dichloromethane at 20℃; for 12h; Stage #2: With boron tribromide In dichloromethane at -78℃; for 5h; Reflux;
90%	With boron tribromide In dichloromethane at -78℃;

52%	Stage #1: 1,3-diphenylisobenzofuran; [1,4]naphthoquinone In dichloromethane at 25℃; for 13h; Stage #2: With boron trifluoride In dichloromethane at -70 - 25℃; for 6.5h; Heating / reflux;	29 6.0 g (22.2 mmol) of 1,3-diphenylisobenzofuran in a powder form was added little by little to a solution, in which 3.51 g (22.2 mmol) of 1,4-naphthoquinone was dissolved in 120 mL of methylene chloride, to obtain a mixed solution. Then, the mixed solution thus obtained was stirred under a light-shielding condition at room temperature (25° C.) for 13 hours. Subsequently, this mixed solution was added with 170 mL of methylene chloride, cooled to -78° C. with dry ice/acetone, and slowly added dropwise with 24 mL (24 mmol) of a 1 M methylene chloride solution of boron tribromide (BBr3). Thereafter, the resultant mixed solution was stirred under a temperature condition of -78° C. for 30 minutes, further stirred at room temperature (25° C.) for 2 hours, and then refluxed for 4 hours to obtain a reaction solution. Subsequently, the reaction solution thus obtained was poured into water and stirred. Thereafter, the aqueous phase and organic phase were separated, and the aqueous phase was extracted with chloroform. After that, the organic phase thus obtained was dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated to obtain a residual solid. The residual solid was recrystallized by using a mixed solvent of chloroform and ethanol (chloroform/ethanol=1/1). Thereby, 6,11-diphenyl-5,12-naphthacenequinone expressed by the following general formula (105) was obtained (a yellow solid: a yield of 4.75 g and 52%). The 6,11-diphenyl-5,12-naphthacenequinone thus obtained was subjected to 1H NMR measurement. Note that, the NMR spectrum was measured with a JOEL JNM EX270 spectrometer (270 MHz for 1H). Moreover, TMS was used as a reference for the chemical shifts in 1H NMR. The measurement result is shown below.1H NMR (CDCl3) δ8.09 (dd, J=5.80, 3.33 Hz, 2H), 7.67 (dd, J=5.90, 2.60, 2H), 7.5-7.61 (m, 8H), 7.51 (dd, J=6.60, 3.30 Hz, 2H), 7.33-7.35 (m, 4H).
	With boron tribromide 1) CH2Cl2, 12h, room temp., 2) CH2Cl2, -78 deg C, 0.5h -> roomtemp., reflux, 4h; Yield given. Multistep reaction;
	Stage #1: 1,3-diphenylisobenzofuran; [1,4]naphthoquinone In dichloromethane for 1h; Stage #2: With boron tribromide In dichloromethane for 0.166667h;	B3.1 Synthesis (B3-1); 100 ml of dichloromethane, 5.2 g of naphthoquinone, and 10 g of 1,3-diphenylisobenzofuran were placed in a 500 ml flask and were stirred for 1 hour. After stirring, 33 ml of commercially available boron tribromide (1 mol/L solution in dichloromethane) was added over 10 minutes, resulting in 7.1 g of yellow needle-shaped crystals (6,11-diphenyl-5,12-naphthacenequinone).
7.1 g	Stage #1: 1,3-diphenylisobenzofuran; [1,4]naphthoquinone In dichloromethane for 1h; Stage #2: With boron tribromide In dichloromethane for 0.166667h;	B3-1 Synthesis (B3-1) To 500 ml Flask, dichloromethane 100 ml and naphthoquinone5.2 g, 1,3-diphenyl isobenzofuran 10g were put and stirred for 1 hour. Afterstirring, boron tribromide (dichloromethane solution 1mol / L) 33ml of commercialproduct was added dropwise over 10 minutes, and yellow needle crystals(6,11-diphenyl- 5,12-Naphthacenequinone) 7.1 g was Obtained.
7.1 g	With boron tribromide In dichloromethane for 0.166667h;	2.B3-1 Flask 500 ml, put and dichloromethane 100 ml, and naphthoquinone 5.2 g, 1,3-diphenyl isobenzofuran 10g, and stirred for 1 hour. After stirring, boron tribromide(dichloromethane solution 1mol / L) 33ml commercial products, by addition over 10 minutes, a yellow needle crystals (6,11-diphenyl-5,12-naphthacenequinone) 7.1 g obtained.
7.1 g	With boron tribromide In dichloromethane for 1h;	B3-1 500 ml flask, 100 ml dichloromethane with, naphthoquinone with 5.2 g, 10 g 1, 3 - [jihueniruisobenzohuran[jihueniruisobenzohuran] filled, stirred for 1 hour. After stirring, the three (1 mol/L solution in dichloromethane) in 33 ml of boron bromide commercially, 10 minutes by the addition of, (6, 11 - diphenyl - 5, 12 - naphthacene quinone) gave 7.1 g yellow needles.

Reference： [1]Location in patent: experimental part Paraskar, Abhimanyu S.; Ravikumar Reddy; Patra, Asit; Wijsboom, Yair H.; Gidron, Ori; Shimon, Linda J.W.; Leitus, Gregory; Bendikov, Michael [Chemistry - A European Journal, 2008, vol. 14, # 34, p. 10639 - 10647]
[2]Wombacher, Tobias; Foro, Sabine; Schneider, Jörg J. [European Journal of Organic Chemistry, 2016, vol. 2016, # 3, p. 569 - 578]
[3]Wombacher, Tobias; Gassmann, Andrea; Foro, Sabine; Von Seggern, Heinz; Schneider, Jörg J. [Angewandte Chemie - International Edition, 2016, vol. 55, # 20, p. 6041 - 6046][Angew. Chem., 2016, vol. 128, # 20, p. 6145 - 6150,6]
[4]Current Patent Assignee: TOYOTA MOTOR CORPORATION; TOYOSHI SHIMADA - US2009/54649, 2009, A1 Location in patent: Page/Page column 40
[5]Dodge, Jeffrey A.; Bain, J. D.; Chamberlin, A. Richard [Journal of Organic Chemistry, 1990, vol. 55, # 13, p. 4190 - 4198]
[6]Current Patent Assignee: SEIKO EPSON CORPORATION - US2012/267615, 2012, A1 Location in patent: Page/Page column 47-48
[7]Current Patent Assignee: SEIKO EPSON CORPORATION - JP2016/6047, 2016, A Location in patent: Paragraph 0207-0208
[8]Current Patent Assignee: SEIKO EPSON CORPORATION - JP2015/71600, 2015, A Location in patent: Paragraph 0103; 0111; 0112; 0113
[9]Current Patent Assignee: SEIKO EPSON CORPORATION - JP6145989, 2017, B2 Location in patent: Paragraph 0135

22
[ 5471-63-6 ]
[ 583-53-9 ]
[ 1499-10-1 ]
[ 15257-17-7 ]
[ 1159-86-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1983,p. 1697 - 1703

23
[ 5471-63-6 ]
[ 85-44-9 ]
[ 1159-86-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 120 % 2: 78%	With monoperoxyphthalic acid In tetrahydrofuran at 25℃;

Reference： [1]Zupancic, Joseph J.; Horn, Keith A.; Schuster, Gary B. [Journal of the American Chemical Society, 1980, vol. 102, # 16, p. 5279 - 5285]

24
[ 5471-63-6 ]
[ 74563-32-9 ]
[ 21596-49-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 35% 2: 39%	With hydrogen In ethyl acetate at 20℃; for 12h;

Reference： [1]Smith, James G.; McCall, Robert B. [Journal of Organic Chemistry, 1980, vol. 45, # 20, p. 3982 - 3986]

25
[ 7267-03-0 ]
[ 5471-63-6 ]
[ 187086-32-4 ]

Yield	Reaction Conditions	Operation in experiment
75%		Intermediate (1) 11 g (0.048 mol), 1,3 - diphenyl iso-benzofuran (1,3-diphenylisobenzofuran) 12.8 g (0.048 mol) in 43.6 ml of Toluene The mixture was stirred under reflux for 16 hours. After distilling off the solvent, it is a 1000 ml Acetic acidAnd heated to 80 . To the mixture, it was added a 48% HBr solution, 132 ml, was stirred for 2 hours under reflux at 80 . roomAfter cooling to-one, the precipitate was collected by filtration, and washed with MeOH. The resulting yellow solid was recrystallized in 100 ml Toluene screendid. By taking the filtered crystal compound (intermediate (2)) 17.5 g (Yield: 75%) of a brown solid was obtained.
75%		Intermediate (1) 11 g (0.048 mol),(1,3-diphenylisobenzofuran) 12.8 g (0.048 mol)A mixture of 43.6 ml of Toluene was stirred under reflux for 16 hours. After distilling off the solvent, Acetic acid was added to 1000 ml, and heated to 80 . To the mixture, it was added 48% HBr Solution 132 ml, was stirred for 2 hours under reflux at 80 . After cooling to room temperature, the precipitate was collected by filtration, and washed with MeOH. The resulting yellow solid was recrystallized with Toluene 100ml. By taking the filtered crystal compound (intermediate (2)) 17.5 g (Yield: 75%) of a brown solid was obtained.
75%	In toluene; for 16h;Reflux;	Intermediate (1) 11 g (0.048mol), 1,3-diphenylisobenzofuran (1,3-diphenylisobenzofuran) 12.8g (0.048 mol) in toluene (Toluene) 43.6ml the mixture was heated under reflux for 16 hours with stirring. After distilling off the solvent, it was added to acetic acid (Acetic acid) 1000ml, and heated to 80C . To the mixture, it was added 48% HBr aqueous solution 132ml, 2 hour at 80C. After cooling to room temperature, the precipitate was collected by filtration and washed with methanol. The resulting yellow solid was recrystallized with toluene (Toluene) 100ml. By taking the filtered crystal compound (intermediate (2)), 17.5g (Yield 75%) of a brown solid was obtained.

74%		(2) Synthesis of 3-bromo-7,12-dibenzo[k]fluoranthene A mixture prepared by adding 14.9 g (55.2 mmol) of 1,3-diphenylisobenzofuran and 12.8 g (55.2 mmol) of 5-bromoacenaphthylene into 50 ml of toluene was stirred while refluxing under heating for 16 h. After distillating away the solvent, adding 1200 ml of acetic acid and the resultant solution was heated up to 80 C. Adding 150 ml of 48 % HBr aqueous solution into the mixture, stirred at 80 C for 1 h. After cooling it down to a room temperature, precipitates were separated by filtration and washed with methanol. The resultant yellow solid was recrystallized through 200 ml of toluene. The crystal was separated by filtration to obtain 19.8 g (yield: 74 %) of yellow solid being 3-bromo-7,12-dibenzo[k]fluoranthene.
74%		Synthesis Example 2 [Synthesis of 3-bromo-7,12-dibenzo[k]fluoranthene] A mixture of 14.9 g (55.2 mmol) of 1,3-diphenylisobenzofuran, 12.8 g (55.2 mmol) of 5-bromoacenaphthylene synthesized in Synthesis Example 1 and 50 mL of toluene was stirred with. heat under reflux for 16 hours. After distillation of the solvent, 1200 mL of acetic acid was added, and the mixture was heated at a temperature of 80C. To the mixture, 150 mL of 48% HBr aqueous solution was added, and the mixture was stirred at a temperature of 80C for one hour. After cooling the mixture to room temperature, precipitates were obtained by filtration and washed with methanol. The resulting yellow solid was recrystallized from 200 mL of toluene. Crystals were obtained by filtration, and 19.8g of 3-bromo-7,12-dibenzo[k]fluoranthene as a yellow solid (yield: 74%).
74%		A mixture of 14.9 g (55.2 mmol) of 1,3-diphenylisobenzofuran and 12.8 g (55.2 mmol) of 5-bromoacenaphthylene in 50 ml of toluene was stirred for 16 hours under heating and reflux. After evaporating the solvent, 1200 ml of acetic acid was added to the mixture, and the mixture was heated to 80C. After the addition of 150 ml of a 48% HBr aqueous solution to the mixture, the mixture was stirred at 80C for 1 hour. After cooling the mixture to room temperature, the precipitate was filtered off, and washed with methanol. The resulting yellow solid was recrystallized from 200 ml of toluene. The resulting crystal was filtered off to obtain 19.8 g of 3-bromo-7,12-diphenylbenzo[k]fluoranthene as a yellow solid (yield: 74%).
74%		A mixture of 14.9 g (55.2 mmol) of 1,3-diphenylisobenzofuran, 12.8 g (55.2 mmol) of 5-bromoacenaphthylene, and 50 mL of toluene was stirred for 16 hours under heat refluxing. After distilling off the solvent, 1,200 mL of acetic acid was added, and the mixture was heated at 80 C. To this mixture, 150 mL of a 48% HBr aqueous solution was added, and the mixture was stirred at 80 C for one hour. After cooling the resultant mixture to room temperature, a precipitate was collected by filtration and washed with methanol. The resulting yellow solid was recrystallized from 200 mL of toluene. A crystal was collected by filtration to obtain 19.8 g (yield: 74%) of 3-bromo-7,12-diphenylbenzo[k]fluoranthene as a yellow solid.
74%		1,3-Diphenylisobenzofuran (14.9 g, 55.2 mmol), 5-bromo camphene (12.8 g,55.2 mmol) in toluene 50 mL was stirred for 16 h. After distilling off the solvent, 1200 mL of acetic acid was added and heated to 80 C. To the mixture was added 150 mL of 48% HBr aqueous solution and the mixture was stirred at 80 C for 1 hour. After cooling to room temperature, the precipitate was filtered off and usedMethanol cleaning. The resulting yellow solid was recrystallized from toluene and the crystals were filtered off to give 3-bromo-7,12-diphenylBenzyl [k] fluoranthene (19.8 g, yield 74%)
74%		Under heating and refluxing,1,3-Diphenylisobenzofuran (14.9 g, 55.2 mmol),5-bromocarbazole(12.8 g, 55.2 mmol) in toluene 50 mL was stirred for 16 h.After distilling off the solvent,Acetic acid 1200 mL was added,Heat to 80 C. To the mixture, 150 mL of a 48% HBr aqueous solution was added,Stir at 80 C for 1 h.After cooling to room temperature,The precipitate was filtered,Wash with methanol.The resulting yellow solid was recrystallized from toluene,Filtered crystals,3-Bromo-7,12-diphenylbenzo [k] fluoranthene (19.8 g, yield 74%) was obtained as a yellow solid
74%		Under heated reflux,1,3-diphenylisobenzofuran (14.9 g, 55.2 mmol),5-bromo-acenaphthylene (12.8g, 55.2mmol)A mixture of 50 mL of toluene was stirred for 16 h.After distilling off the solvent, 1200 mL of acetic acid was added.Heat to 80C.To the mixture was added 150 mL of a 48% aqueous HBr solution.Stirred at 80 C for 1 h.After cooling to room temperature, the precipitate was filtered off and washed with methanol.The resulting yellow solid was recrystallized from toluene and the crystals were collected by filtration to obtain a yellow solid.3-bromo-7,12-diphenylbenzo [k] fluoranthene (19.8 g, yield 74%)
		5 g (18.5 mmol) of diphenylisobenzofuran and 4.3 g (18.5 mmol) of 5-bromoacenaphthylene in toluene were agitated for 24 hours at the reflux temperature. The solvent was distilled off in vacuum, after which the residue was dissolved in 500 ml of acetic acid. An aqueous 40% hydrobromic acid solution, 50 cm3, was added to the solution, which was heated at 80C for one hour. After cooling to room temperature, the precipitate was collected by filtration. This was purified by silica gel chromatography using a mixture of toluene and hexane as an extracting solvent, yielding 7 g of 3-bromo-7,12-diphenylbenzo[k]fluoranthene having a yellowish white color.
9.18 g	With methanesulfonic acid; In 5,5-dimethyl-1,3-cyclohexadiene; at 110 - 150℃; for 8h;	7.67 g (28.37 mmol) of 1,3-diphenylisobenzofuran, 7.72 g (28.40 mmol, 5% bromoacenaphthylene, purity: 85%) and xylene (70 mL) were charged in a reaction vessel, and a 150 C. oil bath For 5 hours.The reaction solution was cooled to 110 C., 0.84 g (8.74 mmol) of methanesulfonic acid was added, and the mixture was heated in an oil bath at 110 C. for 3 hours.The reaction solution was cooled to room temperature and washed with water.Since crystals precipitated, chloroform was added to the organic layer to dissolve the crystals, and the crystals were further washed with water.The combined washings were extracted with chloroform.The organic layers were combined, washed successively with a 5% sodium carbonate aqueous solution and water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure.The residue was subjected to column purification (silica gel · hexane) to obtain 9.18 g of Compound M-1 as yellow crystals.Yield 66.9%.Based on the following data, it was identified as a target compound.

Reference： [1]Patent: KR2015/137230,2015,A .Location in patent: Paragraph 0095; 0096
[2]Patent: KR101581948,2015,B1 .Location in patent: Paragraph 0094; 0098-0099
[3]Patent: KR2016/38310,2016,A .Location in patent: Paragraph 0078; 0079; 0080
[4]Patent: EP2085371,2009,A1 .Location in patent: Page/Page column 49
[5]Patent: EP2495240,2012,A1 .Location in patent: Page/Page column 23
[6]Patent: EP2597094,2013,A1 .Location in patent: Paragraph 0084
[7]Patent: EP2626346,2013,A1 .Location in patent: Paragraph 0152; 0154
[8]Patent: CN107400085,2017,A .Location in patent: Paragraph 0063; 0064; 0067; 0068
[9]Patent: CN107445955,2017,A .Location in patent: Paragraph 0069; 0070; 0073; 0074
[10]Patent: CN107382749,2017,A .Location in patent: Paragraph 0059; 0062; 0063
[11]Journal of Organic Chemistry,1997,vol. 62,p. 530 - 537
[12]Patent: EP1380556,2004,A1 .Location in patent: Page 282
[13]Patent: JP5830967,2015,B2 .Location in patent: Paragraph 0120; 0121

26
[ 5471-63-6 ]
Phenyl[2-(trimethylsilyl)phenyl]iodonium trifluoromethanesulfonate [ No CAS ]
[ 19061-38-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 20℃; for 0.5h;

Reference： [1]Kitamura, Tsugio; Yamane, Masakatsu; Inoue, Kensuke; Todaka, Mitsuru; Fukatsu, Norihiko; Meng, Zhaohong; Fujiwara, Yuzo [Journal of the American Chemical Society, 1999, vol. 121, # 50, p. 11674 - 11679]

27
[ 108-86-1 ]
[ 5471-63-6 ]
[ 19061-38-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With Me₂Zn(TMP)Li In tetrahydrofuran; hexane for 12h; Heating;
100%	With Me₂Zn(TMP)Li In tetrahydrofuran for 12h; Heating;
71%	With bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex In tetrahydrofuran at -78 - 20℃; for 6h; Inert atmosphere;	9,10-Diphenyl-9,10-epoxyanthracene (3a) General procedure: A flame-dried 30-mL two-necked round-bottomed flask equipped with a magneticstirring bar, a rubber septum, and an inlet adapter with three-way stopcock was charged with1,3-diphenylisobenzofuran (2a) (270 mg, 1.00 mmol), dry THF (2.50 mL), and phenyltrifluoromethanesulfonate (79.9 μL, 500 μmol) . After cooling to -78 °C, Mg(TMP)2·2LiCl(0.16 M in THF, 9.5 mL, 1.5 mmol) was added dropwise to the flask and the resultingmixture was stirred at 0 °C for 4 h, after which time TLC (hexanes-dichloromethane = 2:1)indicated complete consumption of phenyl trifluoromethanesulfonate. The reaction wasquenched with 1 M aqueous HCl and the aqueous layer was extracted with ethyl acetate threetimes. The combined organic extracts were successively washed with H2O and brine, driedover anhydrous Na2SO4, and filtered. The organic solvents were removed under reducedpressure to give a crude epoxyanthracene, which was purified by flash silica gel columnchromatography (hexanes-dichloromethane = 2:1) to afford 3a (140.4mg, 405 μmol, 81%) asa white solid. Rf = 0.44 (hexanes-dichloromethane = 2:1). The spectrum data of 3a were incomplete agreement with those reported in the literature.2

Reference： [1]Uchiyama, Masanobu; Miyoshi, Tomoko; Kajihara, Yumiko; Sakamoto, Takao; Otani, Yuko; Ohwada, Tomohiko; Kondo, Yoshinori [Journal of the American Chemical Society, 2002, vol. 124, # 29, p. 8514 - 8515]
[2]Uchiyama, Masanobu; Kobayashi, Yuri; Furuyama, Taniyuki; Nakamura, Shinji; Kajihara, Yumiko; Miyoshi, Tomoko; Sakamoto, Takao; Kondo, Yoshinori; Morokuma, Keiji [Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480]
[3]Miyamoto, Naoya; Nakazawa, Yuki; Nakamura, Takanori; Okano, Kentaro; Sato, Sota; Sun, Zhe; Isobe, Hiroyuki; Tokuyama, Hidetoshi [Synlett, 2018, vol. 29, # 4, p. 513 - 518]

28
[ 108-37-2 ]
[ 5471-63-6 ]
1-chloro-9,10-diphenyl-9,10-epoxyanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With Me₂Zn(TMP)Li In tetrahydrofuran at 20℃; for 48h;

Reference： [1]Uchiyama, Masanobu; Miyoshi, Tomoko; Kajihara, Yumiko; Sakamoto, Takao; Otani, Yuko; Ohwada, Tomohiko; Kondo, Yoshinori [Journal of the American Chemical Society, 2002, vol. 124, # 29, p. 8514 - 8515] Uchiyama, Masanobu; Kobayashi, Yuri; Furuyama, Taniyuki; Nakamura, Shinji; Kajihara, Yumiko; Miyoshi, Tomoko; Sakamoto, Takao; Kondo, Yoshinori; Morokuma, Keiji [Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480]

29
[ 401-78-5 ]
[ 5471-63-6 ]
9,10-diphenyl-2-(trifluoromethyl)-9,10-dihydro-9,10-epoxyanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With Me₂Zn(TMP)Li In tetrahydrofuran at 20℃; for 12h;

Reference： [1]Uchiyama, Masanobu; Miyoshi, Tomoko; Kajihara, Yumiko; Sakamoto, Takao; Otani, Yuko; Ohwada, Tomohiko; Kondo, Yoshinori [Journal of the American Chemical Society, 2002, vol. 124, # 29, p. 8514 - 8515]

30
[ 2398-37-0 ]
[ 5471-63-6 ]
1-methoxy-9,10-diphenyl-9,10-dihydro-9,10-epoxyanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With Me₂Zn(TMP)Li In tetrahydrofuran at 20℃; for 12h;
84%	With bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex In tetrahydrofuran at -78 - 20℃; for 8h; Inert atmosphere;	9,10-Diphenyl-9,10-epoxyanthracene (3a) General procedure: A flame-dried 30-mL two-necked round-bottomed flask equipped with a magneticstirring bar, a rubber septum, and an inlet adapter with three-way stopcock was charged with1,3-diphenylisobenzofuran (2a) (270 mg, 1.00 mmol), dry THF (2.50 mL), and phenyltrifluoromethanesulfonate (79.9 μL, 500 μmol) . After cooling to -78 °C, Mg(TMP)2·2LiCl(0.16 M in THF, 9.5 mL, 1.5 mmol) was added dropwise to the flask and the resultingmixture was stirred at 0 °C for 4 h, after which time TLC (hexanes-dichloromethane = 2:1)indicated complete consumption of phenyl trifluoromethanesulfonate. The reaction wasquenched with 1 M aqueous HCl and the aqueous layer was extracted with ethyl acetate threetimes. The combined organic extracts were successively washed with H2O and brine, driedover anhydrous Na2SO4, and filtered. The organic solvents were removed under reducedpressure to give a crude epoxyanthracene, which was purified by flash silica gel columnchromatography (hexanes-dichloromethane = 2:1) to afford 3a (140.4mg, 405 μmol, 81%) asa white solid. Rf = 0.44 (hexanes-dichloromethane = 2:1). The spectrum data of 3a were incomplete agreement with those reported in the literature.2

Reference： [1]Uchiyama, Masanobu; Miyoshi, Tomoko; Kajihara, Yumiko; Sakamoto, Takao; Otani, Yuko; Ohwada, Tomohiko; Kondo, Yoshinori [Journal of the American Chemical Society, 2002, vol. 124, # 29, p. 8514 - 8515] Uchiyama, Masanobu; Kobayashi, Yuri; Furuyama, Taniyuki; Nakamura, Shinji; Kajihara, Yumiko; Miyoshi, Tomoko; Sakamoto, Takao; Kondo, Yoshinori; Morokuma, Keiji [Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480]
[2]Miyamoto, Naoya; Nakazawa, Yuki; Nakamura, Takanori; Okano, Kentaro; Sato, Sota; Sun, Zhe; Isobe, Hiroyuki; Tokuyama, Hidetoshi [Synlett, 2018, vol. 29, # 4, p. 513 - 518]

31
[ 583-55-1 ]
[ 5471-63-6 ]
[ 19061-38-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With lithium trimethyl zincate In tetrahydrofuran; pentane at -78 - 20℃; for 5h;
96%	With lithium trimethyl zincate In tetrahydrofuran at 0℃; for 5h;

Reference： [1]Uchiyama, Masanobu; Kobayashi, Yuri; Furuyama, Taniyuki; Nakamura, Shinji; Kajihara, Yumiko; Miyoshi, Tomoko; Sakamoto, Takao; Kondo, Yoshinori; Morokuma, Keiji [Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480]
[2]Uchiyama, Masanobu; Miyoshi, Tomoko; Kajihara, Yumiko; Sakamoto, Takao; Otani, Yuko; Ohwada, Tomohiko; Kondo, Yoshinori [Journal of the American Chemical Society, 2002, vol. 124, # 29, p. 8514 - 8515]

32
[ 5471-63-6 ]
[ 17763-67-6 ]
[ 19061-38-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With Me₂Zn(TMP)Li In tetrahydrofuran at 20℃; for 12h;
81%	With bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex In tetrahydrofuran at -78 - 0℃; for 4h; Inert atmosphere;	9,10-Diphenyl-9,10-epoxyanthracene (3a) A flame-dried 30-mL two-necked round-bottomed flask equipped with a magneticstirring bar, a rubber septum, and an inlet adapter with three-way stopcock was charged with1,3-diphenylisobenzofuran (2a) (270 mg, 1.00 mmol), dry THF (2.50 mL), and phenyltrifluoromethanesulfonate (79.9 μL, 500 μmol) . After cooling to -78 °C, Mg(TMP)2·2LiCl(0.16 M in THF, 9.5 mL, 1.5 mmol) was added dropwise to the flask and the resultingmixture was stirred at 0 °C for 4 h, after which time TLC (hexanes-dichloromethane = 2:1)indicated complete consumption of phenyl trifluoromethanesulfonate. The reaction wasquenched with 1 M aqueous HCl and the aqueous layer was extracted with ethyl acetate threetimes. The combined organic extracts were successively washed with H2O and brine, driedover anhydrous Na2SO4, and filtered. The organic solvents were removed under reducedpressure to give a crude epoxyanthracene, which was purified by flash silica gel columnchromatography (hexanes-dichloromethane = 2:1) to afford 3a (140.4mg, 405 μmol, 81%) asa white solid. Rf = 0.44 (hexanes-dichloromethane = 2:1). The spectrum data of 3a were incomplete agreement with those reported in the literature.2

Reference： [1]Uchiyama, Masanobu; Miyoshi, Tomoko; Kajihara, Yumiko; Sakamoto, Takao; Otani, Yuko; Ohwada, Tomohiko; Kondo, Yoshinori [Journal of the American Chemical Society, 2002, vol. 124, # 29, p. 8514 - 8515] Uchiyama, Masanobu; Kobayashi, Yuri; Furuyama, Taniyuki; Nakamura, Shinji; Kajihara, Yumiko; Miyoshi, Tomoko; Sakamoto, Takao; Kondo, Yoshinori; Morokuma, Keiji [Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480]
[2]Miyamoto, Naoya; Nakazawa, Yuki; Nakamura, Takanori; Okano, Kentaro; Sato, Sota; Sun, Zhe; Isobe, Hiroyuki; Tokuyama, Hidetoshi [Synlett, 2018, vol. 29, # 4, p. 513 - 518]

33
[ 5471-63-6 ]
[ 69038-74-0 ]
tert-butyl 9,10-diphenyl-9,10-epoxy-1-anthracenecarboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 8514 - 8515

34
[ 5471-63-6 ]
[ 35309-72-9 ]
1-diisopropylcarbamoyl-9,10-diphenyl-9,10-epoxyanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: N,N-diisopropyl-3-bromobenzamide With Li(2,2,6,6-tetramethylpiperidide)*Al(ⁱBu)₃ In tetrahydrofuran; hexane at 20℃; for 3h; Stage #2: 1,3-diphenylisobenzofuran In tetrahydrofuran; hexane at 20℃; for 18h;
100%	With Li(2,2,6,6-tetramethylpiperidide)*Al(ⁱBu)₃ In tetrahydrofuran; hexane at 20℃; for 18h;
100%	With Me₂Zn(TMP)Li In tetrahydrofuran for 12h; Heating;

Reference： [1]Uchiyama, Masanobu; Naka, Hiroshi; Matsumoto, Yotaro; Ohwada, Tomohiko [Journal of the American Chemical Society, 2004, vol. 126, # 34, p. 10526 - 10527]
[2]Naka, Hiroshi; Uchiyama, Masanobu; Matsumoto, Yotaro; Wheatley, Andrew E. H.; McPartlin, Mary; Morey, James V.; Kondo, Yoshinori [Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 1921 - 1930]
[3]Uchiyama, Masanobu; Miyoshi, Tomoko; Kajihara, Yumiko; Sakamoto, Takao; Otani, Yuko; Ohwada, Tomohiko; Kondo, Yoshinori [Journal of the American Chemical Society, 2002, vol. 124, # 29, p. 8514 - 8515] Uchiyama, Masanobu; Kobayashi, Yuri; Furuyama, Taniyuki; Nakamura, Shinji; Kajihara, Yumiko; Miyoshi, Tomoko; Sakamoto, Takao; Kondo, Yoshinori; Morokuma, Keiji [Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480]

35
[ 5471-63-6 ]
[ 117572-79-9 ]
1-cyano-4-methoxy-9,10-diphenyl-9,10-epoxyanthracene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 8514 - 8515

36
[ 5471-63-6 ]
N,N-diisopropyl-3-bromo-2-iodobenzamide [ No CAS ]
1-diisopropylcarbamoyl-9,10-diphenyl-9,10-epoxyanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With lithium trimethyl zincate In tetrahydrofuran at 0℃; for 5h;

Reference： [1]Uchiyama, Masanobu; Miyoshi, Tomoko; Kajihara, Yumiko; Sakamoto, Takao; Otani, Yuko; Ohwada, Tomohiko; Kondo, Yoshinori [Journal of the American Chemical Society, 2002, vol. 124, # 29, p. 8514 - 8515]

37
[ 574-45-8 ]
[ 100-52-7 ]
[ 5471-63-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With 4 Angstroem MS In toluene at 115℃; for 24h;
93%	With 4 A molecular sieve

Reference： [1]Kuninobu, Yoichiro; Nishina, Yuta; Nakagawa, Chie; Takai, Kazuhiko [Journal of the American Chemical Society, 2006, vol. 128, # 38, p. 12376 - 12377]
[2]Kuninobu, Yoichiro; Nishina, Yuta; Takai, Kazuhiko [Tetrahedron, 2007, vol. 63, # 35, p. 8463 - 8468]

38
[ 7699-79-8 ]
[ 100-52-7 ]
[ 5471-63-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 4 Angstroem MS In toluene at 115℃; for 24h;

Reference： [1]Kuninobu, Yoichiro; Nishina, Yuta; Nakagawa, Chie; Takai, Kazuhiko [Journal of the American Chemical Society, 2006, vol. 128, # 38, p. 12376 - 12377]

39
[ 4122-57-0 ]
phenylmagnesium bromide [ No CAS ]
[ 5471-63-6 ]

Yield	Reaction Conditions	Operation in experiment
65%	In tetrahydrofuran at 20℃;
	Stage #1: 3-methoxy-3H-isobenzofuran-1-one; phenylmagnesium bromide Stage #2: With hydrogenchloride Further stages.;

Reference： [1]Benderradji, Farah; Nechab, Malek; Einhorn, Cathy; Einhorn, Jacques [Synlett, 2006, # 13, p. 2035 - 2038]
[2]Amaladass; Kumar, Natarajan Senthil; Mohanakrishnan, Arasambattu K. [Tetrahedron, 2008, vol. 64, # 34, p. 7992 - 7998]

40
[ 5471-63-6 ]
[ 517-51-1 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4190 - 4198

41
[ 104-92-7 ]
[ 5471-63-6 ]
[ 138738-20-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	With Me₂Zn(TMP)Li In tetrahydrofuran for 72h;
67%	With bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex In tetrahydrofuran at -78℃; for 8h; Inert atmosphere; Reflux;	9,10-Diphenyl-9,10-epoxyanthracene (3a) General procedure: A flame-dried 30-mL two-necked round-bottomed flask equipped with a magneticstirring bar, a rubber septum, and an inlet adapter with three-way stopcock was charged with1,3-diphenylisobenzofuran (2a) (270 mg, 1.00 mmol), dry THF (2.50 mL), and phenyltrifluoromethanesulfonate (79.9 μL, 500 μmol) . After cooling to -78 °C, Mg(TMP)2·2LiCl(0.16 M in THF, 9.5 mL, 1.5 mmol) was added dropwise to the flask and the resultingmixture was stirred at 0 °C for 4 h, after which time TLC (hexanes-dichloromethane = 2:1)indicated complete consumption of phenyl trifluoromethanesulfonate. The reaction wasquenched with 1 M aqueous HCl and the aqueous layer was extracted with ethyl acetate threetimes. The combined organic extracts were successively washed with H2O and brine, driedover anhydrous Na2SO4, and filtered. The organic solvents were removed under reducedpressure to give a crude epoxyanthracene, which was purified by flash silica gel columnchromatography (hexanes-dichloromethane = 2:1) to afford 3a (140.4mg, 405 μmol, 81%) asa white solid. Rf = 0.44 (hexanes-dichloromethane = 2:1). The spectrum data of 3a were incomplete agreement with those reported in the literature.2

Reference： [1]Uchiyama, Masanobu; Kobayashi, Yuri; Furuyama, Taniyuki; Nakamura, Shinji; Kajihara, Yumiko; Miyoshi, Tomoko; Sakamoto, Takao; Kondo, Yoshinori; Morokuma, Keiji [Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480]
[2]Miyamoto, Naoya; Nakazawa, Yuki; Nakamura, Takanori; Okano, Kentaro; Sato, Sota; Sun, Zhe; Isobe, Hiroyuki; Tokuyama, Hidetoshi [Synlett, 2018, vol. 29, # 4, p. 513 - 518]

42
[ 401-78-5 ]
[ 5471-63-6 ]
[ 450412-19-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With Me₂Zn(TMP)Li In tetrahydrofuran at 20℃; for 12h;

Reference： [1]Uchiyama, Masanobu; Kobayashi, Yuri; Furuyama, Taniyuki; Nakamura, Shinji; Kajihara, Yumiko; Miyoshi, Tomoko; Sakamoto, Takao; Kondo, Yoshinori; Morokuma, Keiji [Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480]

43
[ 106-37-6 ]
[ 5471-63-6 ]
[ 642493-24-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With Me₂Zn(TMP)Li In tetrahydrofuran at 20℃; for 13h;

Reference： [1]Uchiyama, Masanobu; Kobayashi, Yuri; Furuyama, Taniyuki; Nakamura, Shinji; Kajihara, Yumiko; Miyoshi, Tomoko; Sakamoto, Takao; Kondo, Yoshinori; Morokuma, Keiji [Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480]

44
[ 92-66-0 ]
[ 5471-63-6 ]
[ 1006715-11-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With Me₂Zn(TMP)Li In tetrahydrofuran at 20℃; for 6h;

Reference： [1]Uchiyama, Masanobu; Kobayashi, Yuri; Furuyama, Taniyuki; Nakamura, Shinji; Kajihara, Yumiko; Miyoshi, Tomoko; Sakamoto, Takao; Kondo, Yoshinori; Morokuma, Keiji [Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480]

45
[ 5471-63-6 ]
[ 66107-32-2 ]
[ 642493-25-2 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 472 - 480

46
[ 5471-63-6 ]
[ 247042-60-0 ]
[ 1006715-08-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex In tetrahydrofuran at -78 - 0℃; for 12h; Inert atmosphere;	9,10-Diphenyl-9,10-epoxyanthracene (3a) General procedure: A flame-dried 30-mL two-necked round-bottomed flask equipped with a magneticstirring bar, a rubber septum, and an inlet adapter with three-way stopcock was charged with1,3-diphenylisobenzofuran (2a) (270 mg, 1.00 mmol), dry THF (2.50 mL), and phenyltrifluoromethanesulfonate (79.9 μL, 500 μmol) . After cooling to -78 °C, Mg(TMP)2·2LiCl(0.16 M in THF, 9.5 mL, 1.5 mmol) was added dropwise to the flask and the resultingmixture was stirred at 0 °C for 4 h, after which time TLC (hexanes-dichloromethane = 2:1)indicated complete consumption of phenyl trifluoromethanesulfonate. The reaction wasquenched with 1 M aqueous HCl and the aqueous layer was extracted with ethyl acetate threetimes. The combined organic extracts were successively washed with H2O and brine, driedover anhydrous Na2SO4, and filtered. The organic solvents were removed under reducedpressure to give a crude epoxyanthracene, which was purified by flash silica gel columnchromatography (hexanes-dichloromethane = 2:1) to afford 3a (140.4mg, 405 μmol, 81%) asa white solid. Rf = 0.44 (hexanes-dichloromethane = 2:1). The spectrum data of 3a were incomplete agreement with those reported in the literature.2
56%	With Me₂Zn(TMP)Li In tetrahydrofuran at 20℃; for 15h;

Reference： [1]Miyamoto, Naoya; Nakazawa, Yuki; Nakamura, Takanori; Okano, Kentaro; Sato, Sota; Sun, Zhe; Isobe, Hiroyuki; Tokuyama, Hidetoshi [Synlett, 2018, vol. 29, # 4, p. 513 - 518]
[2]Uchiyama, Masanobu; Kobayashi, Yuri; Furuyama, Taniyuki; Nakamura, Shinji; Kajihara, Yumiko; Miyoshi, Tomoko; Sakamoto, Takao; Kondo, Yoshinori; Morokuma, Keiji [Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480]

47
[ 108-31-6 ]
[ 5471-63-6 ]
1,4-diphenyl-1,4-epoxy-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylic anhydride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With ethyl acetate for 0.0333333h;	Method B: Liquid-Assisted Grinding; General Procedure General procedure: A mixture of the appropriate diene (1 mmol), dienophile (1mmol), and EtOAc (2-3 drops) was subjected to hand grindingwith a pestle in a mortar for the time shown in Tables 1 and 2. Almost immediately, the color of the mixture changed from fluorescent-green or yellow to white. The EtOAc was removed undervacuum to afford the pure solid product in quantitative yield.
84%	In toluene Heating;
84%	In toluene Heating;

70%	In toluene for 12h; Reflux;
	Heating;

Reference： [1]Agarwal, Jyoti; Rani, Rashmi; Peddinti, Rama Krishna [Synlett, 2017, vol. 28, # 11, p. 1336 - 1340]
[2]Carroll, William R.; Zhao, Chen; Smith, Mark D.; Pellechia, Perry J.; Shimizu, Ken D. [Organic Letters, 2011, vol. 13, # 16, p. 4320 - 4323]
[3]Zhao, Chen; Parrish, Robert M.; Smith, Mark D.; Pellechia, Perry J.; Sherrill, C. David; Shimizu, Ken D. [Journal of the American Chemical Society, 2012, vol. 134, # 35, p. 14306 - 14309]
[4]Maier, Josef M.; Li, Ping; Hwang, Jungwun; Smith, Mark D.; Shimizu, Ken D. [Journal of the American Chemical Society, 2015, vol. 137, # 25, p. 8014 - 8017]
[5]Hwang, Jungwun; Li, Ping; Carroll, William R.; Smith, Mark D.; Pellechia, Perry J.; Shimizu, Ken D. [Journal of the American Chemical Society, 2014, vol. 136, # 40, p. 14060 - 14067]

48
[ 5471-63-6 ]
[ 20776-50-5 ]
[ 201731-79-5 ]

Yield	Reaction Conditions	Operation in experiment
46%	With isopentyl nitrite; In toluene; at 80 - 100℃; for 3h;	EXAMPLE 3; Synthesis of Exemplary Compound A3; Put in 100 mL of toluene were 5.41 g (20 mmol) of E8 and 5.18 g (24 mmol) of E9. After the solution was heated to 80C, 2.81 g (24 mmol) of isoamyl nitrite was gradually added dropwise, and the solution was gradually heated from 80C and was stirred at 100C for three hours. After cooling, the solution was washed twice with 100 mL of water. The organic layer was washed with saturated saline and was dried over magnesium sulfate. The solution was then filtered, and the filtrate was concentrated to yield a dark brown liquid. This was purified by column chromatography (toluene/heptane, 2:3) and was recrystallized fromtoluene/ethanol to yield 3.77 g of E10 (yield: 46%).

Reference： [1]Patent: WO2011/152477,2011,A1 .Location in patent: Page/Page column 36-37

49
[ 5471-63-6 ]
[ 1035806-30-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With bis(dimethyl-di-n-octylammonium) molybdate; dihydrogen peroxide In cyclohexane; lithium hydroxide monohydrate at 25℃; for 2.5h;	Typical catalytic experiments General procedure: [DiC8]2[MoO4] (11.1 mg, 15.8 mol), C8E4 (211.1 mg,0.689 mmol), H2O (1.0 g), cyclohexane (1.0 g) were added consecutively to prepare the microemulsion in a reaction tube. Then-terpinene (50 mg, 0.367 mmol) was added into the mixture and kept at 30C (Winsor IV), the H2O2 (50 wt.%, 17 M) was added stepwise (10 L, each 20 min). The conversion was complete afterthe addition of 6× 10 L (1.02 mmol). Then the reaction tube was kept still at 5C for 3 h, the oil phase was separated and themicroemulsion phase was washed with cyclohexane (1 mL) at 5C, the organic phases were combined and cyclohexane was removed by evaporation, the crude product was purified by asmall chromatography on silica gel (cyclohexane/AcOEt = 5:1) and pure colorless oil was obtained
84%	With dihydrogen peroxide; C₁₀H₁₂INO₄ In tetrahydrofuran; lithium hydroxide monohydrate at 20℃; for 48h;
64%	With tris(2-phenylpyridinato-N,C2′)iridium(III); oxygen In dichloromethane for 48h; Irradiation;	1.1 Preparation of 1,3-diphenylisobenzothiophene 1,3-diphenylisobenzothiophene (DPBT) is a modified method reported by Lin et al. (Hsu et al., J. Org. Chem. 2009, 74, p.9180-91871). , 3-diphenylisobenzofuran (1,3-diphenylisobenzofuran: DPBF) (TCI) was synthesized in two steps (Fig. 2a). Specifically, 1,3-diphenylisobenzofuran (3.70 g, 13.7 mmol) and Irppy (11.3 mg, 13.7 μmol) (Woo et al., J. Am. Chem. Soc. 2013, vol. 135 , p.4771-4787) was added to a 250 mL 1-neck round bottom flask. After adding CH2Cl2 (150 mL) to the flask, the solution was stirred at 365 nm for 2 days under continuous light irradiation and aerobic conditions. The mixture was concentrated in vacuo. Hexane: EtOAc = 3: 1 (v / v) was used as the eluent and column purification was performed with silica gel to obtain 2-benzoylbenzophenone, a white powder, in 64% yield.

	With oxygen Irradiation;
	With oxygen In dimethyl sulfoxide	Quantum yield of ¹O₂ generation The reaction of 1O2 with 1,3-diphenylisobenzofuran (DPBF, Scheme 2) was adopted to evaluate the quantum yield of 1O2 generation by Co(II), Ni(II) and Cu(II) complexes. A sequence of 2 mL of air-saturated DMSO solutions containing DPBF (20 μM) and complexes, of which the absorbance at 470, 458 and 440 nm originating from the absorption of Co(II), Ni(II) and Cu(II) complexes was adjusted to the same (OD470 nm, OD458 nm and OD440 nm = 0.22), were separately charged into an opened 1 cm path quartz cuvette and illuminated with light of 470 nm, 458 nm and 440 nm (obtained from a Shimadzu model impact 1650 UV-visible double beam spectrophotometer, 2.0 nm of slit width). The consumptions of DPBF were followed by monitoring its loss of absorbance at 417 nm (k of irrradiation = 470, 458 and 440 nm) at different irradiation time. [Ru(bpy)3]2+ (bpy = 2,20-bipyridine) was used as standard, whose 1O2 generation quantum yield was determined tobe 0.81 in air saturated methanol
	With C₇₀H₅₀IrN₆⁽¹⁺⁾*Cl^(1-) In ethanol; lithium hydroxide monohydrate Irradiation;
	With oxygen Irradiation;
	With Caswell No_. 744A; singlet oxygen In ethanol; lithium hydroxide monohydrate
	With [7-(dimethylamino)phenothiazin-3-ylidene]dimethylazanium chloride In dimethyl sulfoxide for 0.25h; Irradiation;
	With oxygen In N,N-dimethyl-formamide Irradiation;
	With ultrasound triggered polyethylene glycol coated stanene based nanosheets In aq. phosphate buffer at 21℃;
	With oxygen Sonication;
	With platinum(IV) coordinate carbon dot-titanium dioxide hetrojunction Sonication;	(1) Pt(IV)-CDTiO2-x prepared in Example 4 of the present invention Sonosensitizers can generate large amounts of singlet oxygen (1O2) under low-intensity ultrasound by using 1,3-diphenylisobenzofuran(DPBF) as1O2 Probe to detect Pt(IV)-CDTiO2-x of sonosensitizers under ultrasonic irradiation for 1O2 generation efficiency to evaluate its acoustodynamic performance.

Reference： [1]Hong, Bing; Leclercq, Loïc; Collinet-Fressancourt, Marion; Lai, Jonathan; Bauduin, Pierre; Aubry, Jean-Marie; Nardello-Rataj, Véronique [Journal of Molecular Catalysis A: Chemical, 2015, vol. 397, p. 142 - 149]
[2]Shen, Hui-Jie; Hu, Ze-Nan; Zhang, Chi [Journal of Organic Chemistry, 2022, vol. 87, # 6, p. 3885 - 3894]
[3]Current Patent Assignee: EWHA WOMANS UNIVERSITY - KR102046605, 2019, B1 Location in patent: Paragraph 0058-0062
[4]Pradeepa; Bhojya Naik; Vinay Kumar; Indira Priyadarsini; Barik, Atanu; Ravikumar Naik [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2013, vol. 101, p. 132 - 139]
[5]Pradeepa; Bhojya Naik; Vinay Kumar; Indira Priyadarsini; Barik, Atanu; Ravi Kumarnaik; Prabhakara [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2013, vol. 115, p. 12 - 21]
[6]Xue, Fengfeng; Lu, Yang; Zhou, Zhiguo; Shi, Min; Yan, Yuping; Yang, Hong; Yang, Shiping [Organometallics, 2015, vol. 34, # 1, p. 73 - 77]
[7]Kolemen, Safacan; Işlk; Kim, Gyoung Mi; Kim, Dabin; Geng, Hao; Buyuktemiz, Muhammed; Karatas, Tugce; Zhang, Xian-Fu; Dede, Yavuz; Yoon, Juyoung; Akkaya, Engin U. [Angewandte Chemie - International Edition, 2015, vol. 54, # 18, p. 5340 - 5344][Angew. Chem., 2015, vol. 127, # 18, p. 5351]
[8]Xue, Fengfeng; Shi, Min; Yan, Yuping; Yang, Hong; Zhou, Zhiguo; Yang, Shiping [RSC Advances, 2016, vol. 6, # 19, p. 15509 - 15512]
[9]Chang, Ji-Eun; Liu, Yang; Lee, Tae Heon; Lee, Woo Kyoung; Yoon, Il; Kim, Kwhanmien [International Journal of Molecular Sciences, 2018, vol. 19, # 6]
[10]Lv, Weijie; Chi, Siyu; Feng, Wenqi; Liang, Tao; Song, Dan; Liu, Zhihong [Chemical Communications, 2019, vol. 55, # 49, p. 7037 - 7040]
[11]Chen, Wei; Liu, Chuang; Ji, Xiaoyuan; Joseph, John; Tang, Zhongmin; Ouyang, Jiang; Xiao, Yufen; Kong, Na; Joshi, Nitin; Farokhzad, Omid C.; Tao, Wei; Xie, Tian [Angewandte Chemie - International Edition, 2021, vol. 60, # 13, p. 7155 - 7164][Angew. Chem., 2021, vol. 133, # 13, p. 7231 - 7240,10]
[12]Geng, Bijiang; Xu, Shuang; Li, Ping; Li, Xiaokai; Fang, Fuling; Pan, Dengyu; Shen, Longxiang [Small, 2022, vol. 18, # 6]
[13]Current Patent Assignee: SHANGHAI JIAO TONG UNIVERSITY - CN113648414, 2021, A Location in patent: Paragraph 0028; 0053

50
[ 5398-11-8 ]
[ 100-58-3 ]
[ 5471-63-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: 3-phenylphthalide; phenylmagnesium bromide at -40 - 0℃; Stage #2: With trifluoroacetic acid

Reference： [1]Hamura, Toshiyuki; Nakayama, Ryosuke [Chemistry Letters, 2013, vol. 42, # 9, p. 1013 - 1015]
[2]Johnson, Justin C.; Akdag, Akin; Zamadar, Matibur; Chen, Xudong; Schwerin, Andrew F.; Paci, Irina; Smith, Millicent B.; Havlas, ZdeneÌ¿k; Miller, John R.; Ratner, Mark A.; Nozik, Arthur J.; Michl, Josef [Journal of Physical Chemistry B, 2013, vol. 117, # 16, p. 4680 - 4695]

51
[ 4122-56-9 ]
[ 100-58-3 ]
[ 5471-63-6 ]

Yield	Reaction Conditions	Operation in experiment
85.3%	Stage #1: methyl o-formylbenzoate; phenylmagnesium bromide In tetrahydrofuran at -40 - 0℃; for 1h; Stage #2: With trifluoroacetic acid In tetrahydrofuran at 25℃; for 1.5h;	General Procedure A: Synthesis of Symmetrical Diarylisobenzofuran General procedure: To a solution of methyl 2-formylbenzoate (50.5 mg, 0.308 mmol) in THF (2.0 mL) was added PhMgBr (1.0 M in THF, 0.72 mL, 0.72 mmol) at -40 °C, and the reaction was warmed to 0 °C. After 1 h, CF3CO2H (181 mg, 1.59 mmol) in THF (1 mL) was added to the mixture, and the reaction was stirred at 25 °C for further 1.5 h. The reaction was stopped by adding sat. aq. NaHCO3. The products were extracted with EtOAc (X3), washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by PTLC (hexane/Et2O = 9/1) to gived iphenylisobenzofuran 3a (70.9 mg, 85.3%). Recrystallization from hexane/EtOAc gave 3a as yellow needles.

Reference： [1]Hamura, Toshiyuki; Nakayama, Ryosuke [Chemistry Letters, 2013, vol. 42, # 9, p. 1013 - 1015]

52
[ 5471-63-6 ]
[ 74216-90-3 ]
(1'R*,3S*,8'S*)-1-(4-methylphenyl)-1',8'-diphenyl-11'-oxaspiro[pyrrolidine-3,9'-tricyclo[6.2.1.0(2,7)]undeca-2',4',6'-triene-2,5-dione] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	In dichloromethane at 20℃; for 48h; stereoselective reaction;
46%	In dichloromethane at 20℃; for 48h;	Typical procedure 2 (one-pot procedure): General procedure: A solution of 1,3-diphenylisobenzofuran 2 (1 mmol) and the corresponding imide 1 (1 mmol)in anhydrous CH2Cl2 (10 mL) was magnetically stirred for 48 h at room temperature. MeSO3H (6 mmol) was then added, and the stirring was further maintained for 6h at room temperature. After completion of the reaction (TLC-control) the 10 mL of Na2CO3(aq.) was added carefully to the reaction mixture. The aqueous layer was extracted with CH2Cl2 (3 x 5 mL), the organic layers were combined, dried over MgSO4,and evaporated to dryness. The residue was then purified by preparative thin-layer chromatography using a mixture of hexane/ethyl acetate as eluent.
	In dichloromethane at 20℃; for 48h;	Typical procedure General procedure: A solution of 1,3-diphenylisobenzofuran (2) (1 mmol) and the corresponding imide 1 (1 mmol) in anhydrous dichloromethane (10 mL) was magnetically stirred for 48 h at room temperature. Methanesulfonic acid (6 mmol) was then added and the stirring was further maintained for 6 h at room temperature. After completion of the reaction (TLC control), 10 mL of aq. Na2CO3 was added carefully to the reaction mixture. The aqueous layer was extracted with dichloromethane (3 × 5 mL), the organic layers were combined, dried over MgSO4 and evaporated to dryness. The residue was then purified by preparative thin-layer chromatography using a mixture of hexane/ethyl acetate as eluent.

Reference： [1]Molchanov; Stepakov; Boitsov; Kostikov [Russian Chemical Bulletin, 2013, vol. 62, # 4, p. 1038 - 1041][Izv. Akad. Nauk, Ser. Khim., 2013, vol. 62, # 4, p. 1037 - 1040]
[2]Stepakov, Alexander V.; Boitsov, Vitaly M.; Larina, Anna G.; Molchanov, Alexander P. [Tetrahedron Letters, 2014, vol. 55, # 35, p. 4895 - 4897]
[3]Boitsov; Knyazev; Shmakov; Vyazmin; Nikolaev; Chakchir; Stepakov [Asian Journal of Chemistry, 2019, vol. 31, # 9, p. 2133 - 2138]

53
[ 825-44-5 ]
[ 5471-63-6 ]
[ 1610619-46-9 ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 10234 - 10238
Angew. Chem.,2015,vol. 127,p. 10372 - 10376,5
[2]Organic Letters,2016,vol. 18,p. 384 - 387
[3]Organic Letters,2014,vol. 16,p. 3068 - 3071

54
[ 5471-63-6 ]
[ 792-68-7 ]

Yield	Reaction Conditions	Operation in experiment
	With [NiNP^tBu₃]₄; hydrogen; potassium hydride In toluene at 120℃; for 16h; Inert atmosphere; Sealed tube;	15 Catalytic Hydrodeoxygenation of 1,2-Diphenylisobenzofuran Example 15 Catalytic Hydrodeoxygenation of 1,2-Diphenylisobenzofuran The preparation of reaction mixtures is conducted under an inert atmosphere, for example, in a nitrogen-filled dry box. A Teflon-sealed reactor is charged with 100 mg (0.37 mmol) diphenylisobenzofuran, 10 mg (0.009 mmol) [Ni(NPtBu3)]4, 44 mg (1.10 mmol) KH, 6 mL toluene and a Teflon-sealed magnetic stir bar. The reactor was taken out of the dry box and connected to a hydrogen manifold. The reaction vessel is then charged with H2 (1 atm), employing rigorous inert-atmosphere laboratory techniques. The reaction mixture is then stirred at 1200 rpm for 16 hours in an oil bath at 120° C. The reactor is cooled to room and the reaction mixture quenched with a 10% HCl solution. The organic products are extracted through diethyl ether-water extractions using three 2 mL portions of diethyl ether. The diethyl ether fractions are pooled and subjected to GC-MS analyses. A 95% conversion of the substrate to 1,2-dibenzylbenzene, the completely deoxygenated product, was observed.

Reference： [1]Current Patent Assignee: UNIVERSITY OF ALBERTA - US2014/179954, 2014, A1 Location in patent: Paragraph 0178; 0179

55
[ 5471-63-6 ]
[ 208-96-8 ]
C₃₂H₂₀O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	In o-xylene for 2h; Inert atmosphere; Reflux;	2 Synthesis of Compound [2] Mixed were 14.0 g of acenaphthylene, 25.0 g of diphenylisobenzofuran and 200 ml of o-xylene, and the mixture was heated and refluxed under a nitrogen flow. After 2 hours, the mixture was cooled to room temperature, the solvent was then distilled off, and 300 mL of ether was added. The resultant precipitate was filtered, and vacuum-dried to obtain 27.7 g of an intermediate D (yield: 71%).
71%	In o-xylene for 2h; Reflux; Inert atmosphere;	1 14.0 g of acenaphthylene, 25.0 g of 1,3-diphenylisobenzofuran and 200 ml of o-xylene were mixed, And heated under reflux in a nitrogen stream. After 2 hours, After cooling to room temperature, The solvent was distilled off, Then add ether 300mL. The obtained precipitate was filtered,And vacuum drying, Whereby 27.7 g of intermediate A (71% yield) was obtained.

Reference： [1]Current Patent Assignee: TORAY INDUSTRIES INC - EP2907803, 2015, A1 Location in patent: Paragraph 0135
[2]Current Patent Assignee: TORAY INDUSTRIES INC - TWI558705, 2016, B Location in patent: Paragraph 0138; 0147

56
[ 5471-63-6 ]
2,3,6,7-tetrabromo-9,10-diphenyl-9,10-epoxyanthracene [ No CAS ]
5,7,9,14,16,18-hexaphenyl-5,18:7,16:9,14-triepoxyheptacene [ No CAS ]
2,3-dibromo-5,7,12,14-tetraphenyl-5,14:7,12-diepoxypentacene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 35.4% 2: 23.9%	With n-butyllithium In hexane; toluene at -5 - 25℃; for 0.0833333h;	Typical Procedure for [2+4] Cycloadditions of Aryne and Isobenzofuran: Synthesis of 2,3-Dibromo-9,10-dihydro-9,10-epoxyanthracene (6a) General procedure: To a mixture of 1-bromo-2-iodobenzene (8a, 70.0 mg, 0.247 mmol) and isobenzofuran 1 (71.8 mg, 0.260 mmol) in toluene (2.0 mL) was added n-BuLi (1.60 M in n-hexane, 0.19 mL, 0.30 mmol) at -15 °C, and the reaction was warmed up to 25 °C. After 5 min, the reaction was stopped by adding water. The products were extracted with EtOAc (×3), and the combined organic extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by PTLC (hexane/EtOAc = 8/2) to give 2,3-dibromo-9,10-dihydro-9,10-epoxyanthracene (6a, 67.9 mg, 78.1%) as a white solid and 2,3-dibromo-5,7,12,14-tetrahydro-5,14:7,12-diepoxypentacene (7a, 1.2 mg, 1.0%, ds: 17/83) as a mixture of diastereomers.

Reference： [1]Eda, Shohei; Hamura, Toshiyuki [Molecules, 2015, vol. 20, # 10, p. 19449 - 19462]

57
[ 5471-63-6 ]
2-bromo-3-chloro-5,7,12,14-tetraphenyl-5,14:7,12-diepoxypentacene [ No CAS ]
5,7,9,14,16,18-hexaphenyl-5,18:7,16:9,14-triepoxyheptacene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With n-butyllithium In hexane; toluene at 25℃;	Typical Procedure for [2+4] Cycloadditions of Aryne and Isobenzofuran: Synthesis of 2,3-Dibromo-9,10-dihydro-9,10-epoxyanthracene (6a) General procedure: To a mixture of 1-bromo-2-iodobenzene (8a, 70.0 mg, 0.247 mmol) and isobenzofuran 1 (71.8 mg, 0.260 mmol) in toluene (2.0 mL) was added n-BuLi (1.60 M in n-hexane, 0.19 mL, 0.30 mmol) at -15 °C, and the reaction was warmed up to 25 °C. After 5 min, the reaction was stopped by adding water. The products were extracted with EtOAc (×3), and the combined organic extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by PTLC (hexane/EtOAc = 8/2) to give 2,3-dibromo-9,10-dihydro-9,10-epoxyanthracene (6a, 67.9 mg, 78.1%) as a white solid and 2,3-dibromo-5,7,12,14-tetrahydro-5,14:7,12-diepoxypentacene (7a, 1.2 mg, 1.0%, ds: 17/83) as a mixture of diastereomers.

Reference： [1]Eda, Shohei; Hamura, Toshiyuki [Molecules, 2015, vol. 20, # 10, p. 19449 - 19462]

58
[ 5471-63-6 ]
2,3,6-tribromo-7-chloro-9,10-diphenyl-9,10-epoxyanthracene [ No CAS ]
2-bromo-3-chloro-5,7,12,14-tetraphenyl-5,14:7,12-diepoxypentacene [ No CAS ]
5,7,9,14,16,18-hexaphenyl-5,18:7,16:9,14-triepoxyheptacene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 64.7% 2: 20%	With n-butyllithium In hexane; toluene at -40 - 25℃;	Typical Procedure for [2+4] Cycloadditions of Aryne and Isobenzofuran: Synthesis of 2,3-Dibromo-9,10-dihydro-9,10-epoxyanthracene (6a) General procedure: To a mixture of 1-bromo-2-iodobenzene (8a, 70.0 mg, 0.247 mmol) and isobenzofuran 1 (71.8 mg, 0.260 mmol) in toluene (2.0 mL) was added n-BuLi (1.60 M in n-hexane, 0.19 mL, 0.30 mmol) at -15 °C, and the reaction was warmed up to 25 °C. After 5 min, the reaction was stopped by adding water. The products were extracted with EtOAc (×3), and the combined organic extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by PTLC (hexane/EtOAc = 8/2) to give 2,3-dibromo-9,10-dihydro-9,10-epoxyanthracene (6a, 67.9 mg, 78.1%) as a white solid and 2,3-dibromo-5,7,12,14-tetrahydro-5,14:7,12-diepoxypentacene (7a, 1.2 mg, 1.0%, ds: 17/83) as a mixture of diastereomers.

Reference： [1]Eda, Shohei; Hamura, Toshiyuki [Molecules, 2015, vol. 20, # 10, p. 19449 - 19462]

59
[ 5471-63-6 ]
7-iodo-2-(methylthio)-3-trifluoromethyl-6-triflyloxybenzo[b]furan [ No CAS ]
2-(methylthio)-6,11-diphenyl-3-(trifluoromethyl)anthra[1,2-b]furan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: 1,3-diphenylisobenzofuran; 7-iodo-2-(methylthio)-3-trifluoromethyl-6-triflyloxybenzo[b]furan With (trimethylsilyl)methylmagnesium chloride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: With diiron nonacarbonyl In toluene at 80℃; for 3h; Inert atmosphere;	To a solution of 7-iodo-2-(methylthio)-3-trifluoromethyl-6-triflyloxybenzo[b]furan (1e)(25.3 mg, 50.0 μmol) and 1,3-diphenylisobenzofuran (19) (67.6 mg, 0.250 mmol) dissolvedin THF (0.50 mL) was slowly added (trimethylsilyl)methylmagnesium chloride (0.83 M,THF solution, 0.12 mL, 0.10 mmol) at room temperature. After stirring at the sametemperature for 1 h, to the mixture was added aqueous saturated NH4Cl (0.5 mL). Themixture was extracted with EtOAc (5 mL × 3), and the combined organic extract was washedwith brine (10 mL), dried (Na2SO4), and after filtration, the filtrate was concentrated underreduced pressure. The residue was dissolved in toluene (0.12 mL), and to the solution wasadded nonacarbonyldiiron (53.4 mg, 0.147 mmol). After stirring for 3 h at 80 °C, the mixturewas filtered through a pad of Celite and the filter cake was washed with ethyl acetate. Thefiltrate was concentrated under reduced pressure. The residue was purified by preparativeTLC (n-hexane/CH2Cl2 = 10/1) to give 2-(methylthio)-6,11-diphenyl-3-(trifluoromethyl)anthra[1,2-b]furan (20) (10.9 mg, 22.5 μmol, 45.0% in 2 steps from 1e) as apale yellow solid.

Reference： [1]Morita, Takamoto; Nishiyama, Yoshitake; Yoshida, Suguru; Hosoya, Takamitsu [Chemistry Letters, 2017, vol. 46, # 1, p. 118 - 121]

60
[ 5471-63-6 ]
4-iodo-3-triflyloxydibenzo[b,d]furan [ No CAS ]
5,13-diphenylanthra[1,2-b]benzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	Stage #1: 1,3-diphenylisobenzofuran; 4-iodo-3-triflyloxydibenzo[b,d]furan With (trimethylsilyl)methylmagnesium chloride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: With diiron nonacarbonyl In toluene at 80℃; for 3h; Inert atmosphere;	To a solution of 7-iodo-2-(methylthio)-3-trifluoromethyl-6-triflyloxybenzo[b]furan (1e)(25.3 mg, 50.0 μmol) and 1,3-diphenylisobenzofuran (19) (67.6 mg, 0.250 mmol) dissolvedin THF (0.50 mL) was slowly added (trimethylsilyl)methylmagnesium chloride (0.83 M,THF solution, 0.12 mL, 0.10 mmol) at room temperature. After stirring at the sametemperature for 1 h, to the mixture was added aqueous saturated NH4Cl (0.5 mL). Themixture was extracted with EtOAc (5 mL × 3), and the combined organic extract was washedwith brine (10 mL), dried (Na2SO4), and after filtration, the filtrate was concentrated underreduced pressure. The residue was dissolved in toluene (0.12 mL), and to the solution wasadded nonacarbonyldiiron (53.4 mg, 0.147 mmol). After stirring for 3 h at 80 °C, the mixturewas filtered through a pad of Celite and the filter cake was washed with ethyl acetate. Thefiltrate was concentrated under reduced pressure. The residue was purified by preparativeTLC (n-hexane/CH2Cl2 = 10/1) to give 2-(methylthio)-6,11-diphenyl-3-(trifluoromethyl)anthra[1,2-b]furan (20) (10.9 mg, 22.5 μmol, 45.0% in 2 steps from 1e) as apale yellow solid.

Reference： [1]Morita, Takamoto; Nishiyama, Yoshitake; Yoshida, Suguru; Hosoya, Takamitsu [Chemistry Letters, 2017, vol. 46, # 1, p. 118 - 121]

61
[ 5471-63-6 ]
[ 13380-67-1 ]
2-(4-bromophenyl)-4,9-diphenyl-3a,4,9,9a-tetrahydro-1H-4,9-epoxybenzo[f]isoindole-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With ethyl acetate; for 0.0333333h;	General procedure: A mixture of the appropriate diene (1 mmol), dienophile (1mmol), and EtOAc (2-3 drops) was subjected to hand grindingwith a pestle in a mortar for the time shown in Tables 1 and 2. Almost immediately, the color of the mixture changed from fluorescent-green or yellow to white. The EtOAc was removed undervacuum to afford the pure solid product in quantitative yield. 2-(4-Bromophenyl)-4,9-diphenyl-3a,4,9,9a-tetrahydro-1H-4,9-epoxybenzo[f]isoindole-1,3-dione (5b)White solid; yield: 521 mg (quant); mp 242 C. 1H NMR (500MHz, CDCl3): δ = 8.05 (d, J = 7.5 Hz, 4 H), 7.54 (t, J = 7.5 Hz, 4 H),7.47 (d, J = 7.0 Hz, 2 H), 7.28-7.22 (m, 4 H), 7.05 (dd, J = 3.0, 5.0Hz, 2 H), 6.43 (d, J = 8.5 Hz, 2 H), 4.26 (s, 2 H). 13C NMR (125MHz, CDCl3): δ = 173.0, 144.0, 136.2, 132.1, 130.1, 128.8, 128.7,128.3, 127.9, 127.1, 122.7, 120.8, 90.6, 54.3.

Reference： [1]Synlett,2017,vol. 28,p. 1336 - 1340

62
[ 5471-63-6 ]
[ 670-54-2 ]
C₂₆H₁₄N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With ethyl acetate In ethyl acetate for 0.0166667h;	Method B: Liquid-Assisted Grinding; General Procedure General procedure: A mixture of the appropriate diene (1 mmol), dienophile (1mmol), and EtOAc (2-3 drops) was subjected to hand grindingwith a pestle in a mortar for the time shown in Tables 1 and 2. Almost immediately, the color of the mixture changed from fluorescent-green or yellow to white. The EtOAc was removed undervacuum to afford the pure solid product in quantitative yield.

Reference： [1]Agarwal, Jyoti; Rani, Rashmi; Peddinti, Rama Krishna [Synlett, 2017, vol. 28, # 11, p. 1336 - 1340]

63
[ 5471-63-6 ]
[ 764-42-1 ]
1,4-diphenyl-1,2,3,4-tetrahydro-1,4-epoxynaphthalene-2,3-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With ethyl acetate In ethyl acetate for 0.0666667h;	Method B: Liquid-Assisted Grinding; General Procedure General procedure: A mixture of the appropriate diene (1 mmol), dienophile (1mmol), and EtOAc (2-3 drops) was subjected to hand grindingwith a pestle in a mortar for the time shown in Tables 1 and 2. Almost immediately, the color of the mixture changed from fluorescent-green or yellow to white. The EtOAc was removed undervacuum to afford the pure solid product in quantitative yield.

Reference： [1]Agarwal, Jyoti; Rani, Rashmi; Peddinti, Rama Krishna [Synlett, 2017, vol. 28, # 11, p. 1336 - 1340]

64
[ 5471-63-6 ]
[ 1577232-63-3 ]
diethyl 5-(4-fluorophenyl)-4-((4-fluorophenyl)ethynyl)-6,11-diphenyl-6,11-dihydro-1H-6,11-epoxycyclopenta[a]anthracene-2,2(3H)-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In toluene at 20 - 100℃; for 10h; Inert atmosphere; Schlenk technique;	Typical procedure for the preparation of bridged heterocycles. General procedure: Tetraynes (1.0 equiv) and 2 (1.1 equiv) were added to toluene (2.0 mL), the mixture was stirred at room temperature then heated at 100 °C for 10 h in air. The reaction mixture was cooled to room temperature, and the solvent was evaporated in vacuo. The residue was purified by preparative thin layer chromatography (TLC) on silica gel with the appropriate mixture of petroleum ether and EtOAc to give the desired product.

Reference： [1]Meng, Xiangzhen; Cheng, Dong; Lv, Shuang; Ma, Jie; Hu, Yimin [Heterocycles, 2017, vol. 94, # 11, p. 2111 - 2124]

65
[ 5471-63-6 ]
C₂₇H₁₈F₂O₄ [ No CAS ]
dimethyl 5-(4-fluorophenyl)-4-((4-fluorophenyl)ethynyl)-6,11-diphenyl-6,11-dihydro-1H-6,11-epoxycyclopenta[a]anthracene-2,2(3H)-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In toluene at 20 - 100℃; for 10h; Inert atmosphere; Schlenk technique;	Typical procedure for the preparation of bridged heterocycles. General procedure: Tetraynes (1.0 equiv) and 2 (1.1 equiv) were added to toluene (2.0 mL), the mixture was stirred at room temperature then heated at 100 °C for 10 h in air. The reaction mixture was cooled to room temperature, and the solvent was evaporated in vacuo. The residue was purified by preparative thin layer chromatography (TLC) on silica gel with the appropriate mixture of petroleum ether and EtOAc to give the desired product.

Reference： [1]Meng, Xiangzhen; Cheng, Dong; Lv, Shuang; Ma, Jie; Hu, Yimin [Heterocycles, 2017, vol. 94, # 11, p. 2111 - 2124]

66
[ 5471-63-6 ]
C₂₇H₁₈Cl₂O₄ [ No CAS ]
dimethyl 5-(4-chlorophenyl)-4-((4-chlorophenyl)ethynyl)-6,11-diphenyl-6,11-dihydro-1H-6,11-epoxycyclopenta[a]anthracene-2,2(3H)-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In toluene at 20 - 100℃; for 10h; Inert atmosphere; Schlenk technique;	Typical procedure for the preparation of bridged heterocycles. General procedure: Tetraynes (1.0 equiv) and 2 (1.1 equiv) were added to toluene (2.0 mL), the mixture was stirred at room temperature then heated at 100 °C for 10 h in air. The reaction mixture was cooled to room temperature, and the solvent was evaporated in vacuo. The residue was purified by preparative thin layer chromatography (TLC) on silica gel with the appropriate mixture of petroleum ether and EtOAc to give the desired product.

Reference： [1]Meng, Xiangzhen; Cheng, Dong; Lv, Shuang; Ma, Jie; Hu, Yimin [Heterocycles, 2017, vol. 94, # 11, p. 2111 - 2124]

67
[ 5471-63-6 ]
[ 187086-32-4 ]

Reference： [1]Patent: JP6244634,2017,B2

68
[ 5471-63-6 ]
[ 125261-30-5 ]
ethyl 9,10-diphenyl-9,10-epoxy-2-anthracenecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex In tetrahydrofuran at -78 - 20℃; for 5h; Inert atmosphere;	9,10-Diphenyl-9,10-epoxyanthracene (3a) General procedure: A flame-dried 30-mL two-necked round-bottomed flask equipped with a magneticstirring bar, a rubber septum, and an inlet adapter with three-way stopcock was charged with1,3-diphenylisobenzofuran (2a) (270 mg, 1.00 mmol), dry THF (2.50 mL), and phenyltrifluoromethanesulfonate (79.9 μL, 500 μmol) . After cooling to -78 °C, Mg(TMP)2·2LiCl(0.16 M in THF, 9.5 mL, 1.5 mmol) was added dropwise to the flask and the resultingmixture was stirred at 0 °C for 4 h, after which time TLC (hexanes-dichloromethane = 2:1)indicated complete consumption of phenyl trifluoromethanesulfonate. The reaction wasquenched with 1 M aqueous HCl and the aqueous layer was extracted with ethyl acetate threetimes. The combined organic extracts were successively washed with H2O and brine, driedover anhydrous Na2SO4, and filtered. The organic solvents were removed under reducedpressure to give a crude epoxyanthracene, which was purified by flash silica gel columnchromatography (hexanes-dichloromethane = 2:1) to afford 3a (140.4mg, 405 μmol, 81%) asa white solid. Rf = 0.44 (hexanes-dichloromethane = 2:1). The spectrum data of 3a were incomplete agreement with those reported in the literature.2