Name: 5388-42-1|2-Phenylisoindolin-1-one|97%
Brand: Ambeed
SKU: A801405
Price: 40.0 USD
Availability: InStock
Rating: 92 (40 reviews)

1
[ 520-03-6 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With ethanol; tetrabutylammonium tetrafluoroborate; diisopropylamine at 20℃; for 3h; Electrochemical reaction; Schlenk technique; Green chemistry; chemoselective reaction;
	With hydrogenchloride; tin
	With ethanol; sulfuric acid; water at 85℃; Bei der elektrochemischen Reduktion an einer Blei-Kathode;

	With hydrogenchloride; samarium diiodide 1.) THF, ca. 20 deg C, 15 min, 2.) THF; Yield given. Multistep reaction;
36 %Chromat.	With cobalt(II) bis[bis((trifluoromethyl)sulfonyl)amide]; trimethylsilyl trifluoromethanesulfonate; (p-anisyl)triphos; hydrogen In n-heptane at 125℃; for 18h; Autoclave; Sealed tube;

Reference： [1]Bai, Ya; Shi, Lingling; Zheng, Lianyou; Ning, Shulin; Che, Xin; Zhang, Zhuoqi; Xiang, Jinbao [Organic Letters, 2021, vol. 23, # 6, p. 2298 - 2302]
[2]Graebe; Pictet [Justus Liebigs Annalen der Chemie, 1888, vol. 247, p. 302]
[3]Sakurai [Bulletin of the Chemical Society of Japan, 1930, vol. 5, p. 184,188]
[4]Brandukova; Vygodskii; Komarova; Strelkova [Russian Chemical Bulletin, 1996, vol. 45, # 5, p. 1176 - 1177]
[5]Papa, Veronica; Cabrero-Antonino, Jose R.; Spannenberg, Anke; Junge, Kathrin; Beller, Matthias [Catalysis science and technology, 2020, vol. 10, # 18, p. 6116 - 6128]

2
[ 87-41-2 ]
[ 62-53-3 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With indium(III) chloride at 200℃; for 6h; Inert atmosphere;	Typical Experimental Procedure for the Preparation of Phthalimidine Aniline (0.182 mL, d = 1.022, 2.0 mmol) was added to the reaction flask containing phthalide (0.134 g, 1.0 mmol) and InCl3(0.0442 g, 0.2 mmol) under Ar atmosphere over ca. 3 min with stirring, and the whole mixture was heated at gentle reflux utilizing an oil bath (200 oC) for 12 h. During the rise of temperature, powdered phthalide melted off and fully mixed with aniline. On the other hand, InCl3 partially dissolved to keep the mixture as a suspension throughout the reaction period. Then, the reaction mixture was cooled to room temperature and poured onto ice-cold 1 % HCl, and then extracted with EtOAc. Organic layer was washed by satd. aq. NaHCO3, dried over anhyd. MgSO4, and then filtered. Evaporation gave acrude product, which was purified by column chromatography (silica gel, eluted by hexane-EtOAc) to give pure 2-phenylphthalimidine (0.190 g, 91 %). Other phthalimidine derivatives in the present work were prepared from the combination between appropriate phthalide and primary amine using the similar procedure to that described above. Two 2-(nitrophenyl)-phthaliimidines (trace yields) were merely subjected to 1H NMR spectral comparisons with those of authentic samples previously prepared by us (references 3 and 8 of the main text).
95%	With gallium(III) trichloride In neat (no solvent) at 200℃; for 12h; Inert atmosphere;
	at 200 - 220℃;

Reference： [1]Takahashi, Ichiro; Matsunaga, Takatoshi; Izumi, Yuuki; Sunada, Yuuki; Kawakami, Nanae; Horino, Yuusuke; Inagaki, Sho; Saitoh, Kenta; Hatanaka, Minoru; Hosoi, Shinzo [Letters in Organic Chemistry, 2017, vol. 14, # 3, p. 153 - 158]
[2]Takahashi, Ichiro; Nishiwaki, Yoshinori; Saitoh, Kenta; Matsunaga, Takatoshi; Aratake, Akihiro; Morita, Toshio; Hosoi, Shinzo [Heterocycles, 2019, vol. 99, # 1, p. 222 - 237]
[3]Hessert [Chemische Berichte, 1877, vol. 10, p. 1450][Chemische Berichte, 1878, vol. 11, p. 239]

3
[ 5388-42-1 ]
[ 4770-74-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; potassium nitrate

Reference： [1]Borsche et al. [Chemische Berichte, 1934, vol. 67, p. 675,681]

4
[ 5388-42-1 ]
[ 73357-35-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With lithium dihydrido-bis(2-methoxyethoxo)aluminate In toluene at 20℃;
	With lithium aluminium tetrahydride; diethyl ether
92 %Spectr.	With diphenylsilane; potassium <i>tert</i>-butylate In 1,4-dioxane at 110℃; Inert atmosphere; Schlenk technique;

Reference： [1]Kovtunenko, V. A.; Kucherenko, T. T.; Kornilov, M. Yu.; Tyltin, A. K.; Turov, A. V.; Babichev, F. S. [Chemistry of Heterocyclic Compounds, 1987, vol. 23, # 12, p. 1308 - 1311][Khimiya Geterotsiklicheskikh Soedinenii, 1987, # 12, p. 1629 - 1631]
[2]Wittig et al. [Justus Liebigs Annalen der Chemie, 1955, vol. 594, p. 89,111]
[3]Ding, Guangni; Wu, Xiaoyu; Jiang, Lili; Zhang, Zhaoguo; Xie, Xiaomin [Organic Letters, 2017, vol. 19, # 22, p. 6048 - 6051]

5
[ 62-53-3 ]
[ 643-79-8 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	In N,N-dimethyl-formamide; acetonitrile at 20℃;
66%	With 1,2,3-Benzotriazole; 2-hydroxyethanethiol In acetonitrile at 20℃; for 13h; Inert atmosphere;	Preparation of 2-[p-(N,N-Diethylamino)phenyl]phthalimidine (1) General procedure: To a solution of o-phthaldehyde (OPT; 1.341 g, 10 mmol) in MeCN (30 mL) was added successively (i) a solution of 2-mercaptoethanol (MET; 6.0 mL, 86 mmol) in MeCN (10 mL) over 3 min, (ii) a solution of N,N-diethylphenylenediamine (1.720 g, 10 mmol) in MeCN (10 mL) over 2 min, (iii)1,2,3-1H-benzotriazole (1.191 g, 10 mmol) portionwise over 2 min, and (iv) pH 9.6 buffer (0.05 MH3BO3-KCl-NaOH; 5 mL) over 3 min with stirring at room temperature. After the additions were complete, the mixture was further stirred at room temperature for 13 h under N2., and then evaporated. After storage in refrigerator for 3 h, the resulting solids were filtered, washed successively with ice-cold Et2O and water, and then dried in vacuo to give crude phthalimidine (1.956 g, mp 145-206 oC). The filtrate was evaporated and diluted with water (100 mL). The further resulting solids were filtered,washed successively with ice-cold Et2O and water, and then dried in vacuo to give another crop of crude product (0.376 g, mp 142-224 oC). Both of the crude samples were combined (2.432 g, 87%) andsubjected to recrystallization from MeOH to give the analytically pure sample of2-[4-(N,N-diethylamino)phenyl]phthalimidine (1; 2.094 g, 72%, mp 149-152 oC) as lemon-yellow needles. Compounds 3-7, 9-16, 21, 22, 24, and 30 were also prepared from the corresponding primary amines using the similar procedure to that described above. In cases of compounds 2 and 8, precipitates appeared during 13 h reaction time, so the reaction mixture was first filtered to collect crude phthalimidine, followed by the work-up described above.
50%	With acetic acid In ethyl acetate at 20℃; for 3h;

	With diethyl ether
	With acetic acid for 0.333333h; Heating;
	With acetic acid Yield given;

Reference： [1]Wan, Jieping; Wu, Bin; Pan, Yuanjiang [Tetrahedron, 2007, vol. 63, # 38, p. 9338 - 9344]
[2]Takahashi, Ichiro; Kawakami, Teruki; Hirano, Etsushi; Kimino, Mako; Kamimura, Shigeki; Miwa, Takayuki; Tamura, Takanori; Tazaki, Ryo; Kitajima, Hidehiko; Hatanaka, Minoru; Isa, Kimio; Hosoi, Shinzo [Heterocycles, 2016, vol. 93, # 2, p. 557 - 571]
[3]Lewis, Frederick D.; Liu, Weizhong [Journal of Physical Chemistry A, 2002, vol. 106, # 10, p. 1976 - 1984]
[4]Thiele; Schneider [Justus Liebigs Annalen der Chemie, 1909, vol. 369, p. 293]
[5]Azumaya, Isao; Kagechika, Hiroyuki; Fujiwara, Yoshihisa; Itoh, Michiya; Yamaguchi, Kentaro; Shudo, Koichi [Journal of the American Chemical Society, 1991, vol. 113, # 8, p. 2833 - 2838]
[6]Grigg, Ronald; Gunaratne, H. Q. Nimal; Sridharan, Visuvanathar [Journal of the Chemical Society. Chemical communications, 1985, # 17, p. 1183 - 1184]

6
[ 5388-42-1 ]
[ 89313-76-8 ]

Yield	Reaction Conditions	Operation in experiment
53%	With pyridine; diphosphorus pentasulfide at 140 - 150℃;
	With Lawessons reagent In toluene Heating;

Reference： [1]Kovtunenko, V. A.; Dobrenko, T. T.; Voitenko, Z. V.; Tyltin, A. K.; Babichev, F. S. [Chemistry of Heterocyclic Compounds, 1984, vol. 20, # 9, p. 978 - 983][Khimiya Geterotsiklicheskikh Soedinenii, 1984, vol. 20, # 9, p. 1200 - 1205]
[2]Nishio, Takehiko; Okuda, Norikazu [Journal of Organic Chemistry, 1992, vol. 57, # 14, p. 4000 - 4005]

7
[ 33238-23-2 ]
[ 5388-42-1 ]
[ 66614-81-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 55% 2: 35%	With sodium acetate In ethylene glycol for 1h; Heating;

Reference： [1]Scartoni; Tognetti [Journal of Heterocyclic Chemistry, 1984, vol. 21, # 5, p. 1499 - 1503]

8
[ 201230-82-2 ]
[ 50844-92-3 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium ethanolate In ethanol at 35℃;

Reference： [1]Foa, M.; Francalanci, F.; Bencini, E.; Gardano, A. [Journal of Organometallic Chemistry, 1985, vol. 285, p. 293 - 304]

9
3a,4-dihydro-1-oxo-4-phenylisoindoline [ No CAS ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	In xylene for 24h; Heating;

Reference： [1]Noguchi, Michihiko; Kakimoto, Shinji; Kawakami, Hisao; Kajigaeshi, Shoji [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 5, p. 1355 - 1362]

10
(E)-N-benzylidenebenzenamine [ No CAS ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	With dicobalt octacarbonyl; benzene at 230℃;
	With dicobalt octacarbonyl; benzene at 325℃;

Reference： [1]Murahashi; Horiie [1959, vol. 7, p. 89,93] Murahashi et al. [Nippon Kagaku Zasshi, 1958, vol. 79, p. 68,79][Chem.Abstr., 1960, p. 5558]
[2]Current Patent Assignee: DUPONT DE NEMOURS INC - US2841591, 1952, A

11
[ 5388-42-1 ]
[ 7664-93-9 ]
[ 4770-74-5 ]

Reference： [1]Borsche et al. [Chemische Berichte, 1934, vol. 67, p. 675,681]

12
[ 59473-45-9 ]
[ 103-71-9 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: 2-(chloromethyl)iodobenzene With isopropylmagnesium bromide In tetrahydrofuran at -30℃; for 1h; Stage #2: phenyl isocyanate In tetrahydrofuran at -20 - 20℃; for 2h; Further stages.;

Reference： [1]Delacroix; Berillon; Cahiez; Knochel [Journal of Organic Chemistry, 2000, vol. 65, # 23, p. 8108 - 8110]

13
[ 33966-11-9 ]
[ 27711-59-7 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 2-(hydroxymethyl)-N-phenylbenzamide With isopropylmagnesium chloride In tetrahydrofuran at 50℃; Stage #2: With N,N,N',N'-Tetramethylphosphorodiamidic chloride In tetrahydrofuran at 50℃;

Reference： [1]Tsuritani, Takayuki; Kii, Satoshi; Akao, Atsushi; Sato, Kimihiko; Nonoyama, Nobuaki; Mase, Toshiaki; Yasuda, Nobuyoshi [Synlett, 2006, # 5, p. 801 - 803]

14
[ 87-41-2 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: AlCl₃ / 1,2-dichloro-ethane 2.1: i-PrMgCl / tetrahydrofuran; various solvent(s) / 50 °C 2.2: 70 percent / ClP(O)(NMe₂)2 / tetrahydrofuran; various solvent(s) / 50 °C
	Multi-step reaction with 3 steps 1: xylene; phosphorus (V)-sulfide 2: aniline / 190 °C 3: 240 °C
	Multi-step reaction with 3 steps 1: chlorine; triphenylphosphine / dichloromethane / 0.08 h / Microwave irradiation 2: triethylamine / dichloromethane / 2.5 h / 20 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 20 °C

Reference： [1]Tsuritani, Takayuki; Kii, Satoshi; Akao, Atsushi; Sato, Kimihiko; Nonoyama, Nobuaki; Mase, Toshiaki; Yasuda, Nobuyoshi [Synlett, 2006, # 5, p. 801 - 803]
[2]Prey; Kondler [Monatshefte fur Chemie, 1958, vol. 89, p. 505,507]
[3]Pietka-Ottlik, Magdalena; Potaczek, Piotr; Piasecki, Egbert; Mlochowski, Jacek [Molecules, 2010, vol. 15, # 11, p. 8214 - 8228]

15
[ 589-09-3 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 60 percent / Et₃N / tetrahydrofuran / 12 h / Ambient temperature 2: 99 percent / hexane / Heating 3: 98 percent / 10percent Pd/C / xylene / 24 h / Heating

Reference： [1]Noguchi, Michihiko; Kakimoto, Shinji; Kawakami, Hisao; Kajigaeshi, Shoji [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 5, p. 1355 - 1362]

16
[ 75611-67-5 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 60 percent / Et₃N / tetrahydrofuran / 12 h / Ambient temperature 2: 99 percent / hexane / Heating 3: 98 percent / 10percent Pd/C / xylene / 24 h / Heating

Reference： [1]Noguchi, Michihiko; Kakimoto, Shinji; Kawakami, Hisao; Kajigaeshi, Shoji [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 5, p. 1355 - 1362]

17
[ 612-20-4 ]
[ 5388-42-1 ]

Reference： [1]Chemische Berichte,1877,vol. 10,p. 1450
Chemische Berichte,1878,vol. 11,p. 239

18
[ 5388-42-1 ]
[ 75-36-5 ]
[ 60025-40-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	With hydrogenchloride In carbon disulfide	1 4-(1-oxo-2-isoindolinyl) acetophenone EXAMPLE 1 4-(1-oxo-2-isoindolinyl) acetophenone To a stirred suspension of N-phenylphthalimidine (20.9 g) in carbon disulfide (400 ml), is added acetyl chloride (13.3 g) at room temperature and the mixture is vigorously stirred while aluminum chloride (39.9 g) is added to this mixture in small portions. The whole mixture is refluxed for 4 hours, allowed to stand overnight and further refluxed for 6 hours. After cooling, the organic layer is decanted and the resulting reddish oil is poured into ice cooled 10% hydrochloric acid (300 ml). The percipitated crystals are collected by filtration, washed with water and dried. Recrystallization from ethanol-chloroform gives pale yellow needles (20.6 g, 82%). Melting point: 243° to 244° C. Elementary analysis calculated for C16 H13 NO2: C, 76.47; H, 5.22; N, 5.57. Found: C, 76.25; H, 5.24; N, 5.61. NMR (CDCl3) δ: 2.60 (3H, singlet, CH3). 4.93 (2H, singlet, CH2 N). 7.5 to 8.2(8H, multiplet, ArH). Mass spectrum (m/e): 251 (M+).

Reference： [1]Current Patent Assignee: ASKA PHARMACEUTICAL CO., LTD. - US4166125, 1979, A

19
[ 201230-82-2 ]
[ 62-53-3 ]
[ 6630-33-7 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
81%	With bis(benzonitrile)palladium(II) dichloride; triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 24h; Autoclave;

Reference： [1]Location in patent: body text Cho, Chan Sik; Ren, Wen Xiu [Tetrahedron Letters, 2009, vol. 50, # 18, p. 2097 - 2099]

20
[ 1234559-97-7 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; potassium carbonate In N,N-dimethyl acetamide at 120℃; for 2h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Zheng, Yu; Yu, Gongli; Wu, Jinlong; Dai, Wei-Min [Synlett, 2010, # 7, p. 1075 - 1080]

21
[ 201230-82-2 ]
[ 40400-13-3 ]
[ 62-53-3 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 50℃; for 48h; chemoselective reaction;	4.2. Cycloaminocarbonylation of 2-iodobenzyl bromide (1) in the presence of primary amines under atmospheric carbon monoxide pressure General procedure: In a typical experiment Pd(OAc)2 (5.6 mg, 0.025 mmol), PPh3 (13.1 mg, 0.05 mmol), 2-iodobenzyl bromide (297 mg,1 mmol), 6 mmol of tert-butylamine (0.63 mL, 6 mmol or 2.2 mmol of amino acid methylester hydrochloride) and 0.5 mL triethylamine were dissolved in DMF (10 mL) under argon in a 100 mL three-necked flask equipped with a gas inlet, reflux condenser with a balloon at the top. The atmosphere was changed to carbon monoxide. The reaction was conducted for the given reaction time upon stirring at 50 °C and analysed by GC-MS. The mixture was then concentrated and evaporated to dryness. The residue was dissolved in chloroform (20 mL) and washed with water (20 mL). The organic phase was thoroughly washed twice with 5% HCl (20 mL), saturated NaHCO3 (20 mL), brine (20 mL), dried over Na2SO4 and concentrated to powder-like crystalline material in case of 2a-c or to a waxy residue in case of 2d,e. All compounds were subjected to column chromatography under the conditions indicated in Section 4.5.

Reference： [1]Location in patent: experimental part Marosvölgyi-Haskó, Diána; Takács, Attila; Riedl, Zsuzsanna; Kollár, László [Tetrahedron, 2011, vol. 67, # 5, p. 1036 - 1040]

22
[ 13169-52-3 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 2h;

Reference： [1]Location in patent: experimental part Pietka-Ottlik, Magdalena; Potaczek, Piotr; Piasecki, Egbert; Mlochowski, Jacek [Molecules, 2010, vol. 15, # 11, p. 8214 - 8228]

23
[ 62-53-3 ]
[ 119-67-5 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With formic acid; triethylamine In ethanol at 80℃; for 1h;
98%	With (dipyridylamine)Cp*IrOSO₃; hydrogen In neat (no solvent) at 110℃; for 16h; Autoclave; chemoselective reaction;
98%	With 1,4-diaza-bicyclo[2.2.2]octane; formic acid; palladium diacetate In 1,4-dioxane at 80℃; for 3h; Inert atmosphere;

96%	With (2,6-dichlorophenyl)bis(2,3,5,6-tetrafluorophenyl)borane; hydrogen In tetrahydrofuran at 100℃; for 6h; Sealed tube; Molecular sieve; Autoclave; Green chemistry;
96%	With formic acid; C₂₂H₂₉IrN₄O₄S In water at 60℃; for 17h; Schlenk technique;
95%	With hydrogen In toluene at 90℃; for 14h; Autoclave;
95%	With tris(pentafluorophenyl)borate; phenylsilane In toluene at 120℃; for 1.5h;	4.2. Typical procedures General procedure: The reductive amination of LA and aniline was performed in a thick wall tube with a Teflon screw cap (10 mL volume). In a typical experiment, under air atmosphere, 0.25 mmol LA, 0.25 mmol aniline, 2.5 mol% B(C6F5)3 and 1 mL toluene were added into the reactor. One or three equiv. PhSiH3 was used for the synthesis of pyrrolidone or pyrrolidine respectively. Then, the reactor was heated in oil bath for the desired time. Upon the completion of reaction, the product yield was determined by HPLC with standard curves of pure products. The pure samples were isolated by column chromatography on silica gel with the eluent (petroleum ether:ethyl acetate = 1:1) for pyrrolidones and (petroleum ether: ethyl acetate = 10:1) for pyrrolidines.
94%	With carbon monoxide; water In tetrahydrofuran at 120℃; for 12h;
94%	With carbon monoxide In tetrahydrofuran; water at 120℃; for 12h;	38 Referring to Equation 2, when 2-formylbenzoic acid is reacted with aniline, isoindolin-1-one is reacted with a high In particular, when 4-methoxyaniline was used as the reaction substrate, a high yield of 98% was obtained. The melting point, NMR and gas chromatography mass spectrometry results of the amine compound prepared in Example 38 are as follows.
94%	With 1,4-diaza-bicyclo[2.2.2]octane; formic acid; palladium diacetate In 1,4-dioxane at 80℃; for 1h;	General procedure for the synthesis of compounds 3 General procedure: A mixture of 2-formylbenzoic acid (1) (2.0 mmol), amine (2) (2.4 mmol, 1.2 equiv), DABCO (448 mg, 2 equiv), HCOOH (0.5 mL), Pd(OAc)2 (22.5 mg, 0.1 mmol, 5 mol%) in 1,4-dioxane (2 mL) was heated to 80 oC for an appropriate time (Table 3). After completion of the reaction, the mixture was cooled to room temperature, and diluted with DCM (20 mL). The solid was removed by filter, and the filtrate was washed with water (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/acetone = 5/1, v/v) to afford the product 3.
92%	With cobalt(II) phthalocyanine; diphenylsilane In ethanol at 70℃; for 12h; chemoselective reaction;
92%	With cobalt(II) phthalocyanine; diphenylsilane In ethanol at 20 - 70℃; for 6h; Green chemistry; chemoselective reaction;
92%	Stage #1: aniline; o-carboxybenzaldehyde With tris(pentafluorophenyl)borate In 1,2-dichloro-benzene for 0.25h; Stage #2: With Dimethylphenylsilane; tris(pentafluorophenyl)borate at 100℃; for 1h;
86%	With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In dichloromethane at 20℃; for 5h; Inert atmosphere;	2.Typical procedure for the synthesis of N-substituted isoindolinones: General procedure: A mixture of 2-formylbenzoic acid (1.0 mmol), amine (1.1 mmol), and Hantzsch ester (1.2 mmol) was stirred in CH2Cl2 (3 mL) at room temperature under N2 until the reaction was complete (TLC analysis). A solution of saturated NaHCO3 (5 mL) was added, and was extracted with EtOAc (3×10 mL). The combined organic layers were dried over anhydrous MgSO4 and concentrated to give a residue that was purified by column chromatography with EtOAc/petroleum (1:10-1:3) as an eluent. 3. Characterization data of Products 2-Phenylisoindolin-1-one(3a) [1]: White solid; 180 mg, yield: 86%; m.p.: 162-163. 1H NMR (400 MHz, Chloroform-d) δ 7.93 (d, J = 7.4 Hz, 1H), 7.89 - 7.86 (m, 2H), 7.62 - 7.58 (m, 1H), 7.51 (t, J = 7.6 Hz, 2H), 7.45 - 7.41 (m, 2H), 7.18 (t, J = 7.2 Hz, 1H), 4.86 (s, 2H).
80%	With aluminum (III) chloride In ethanol at 25 - 70℃; Inert atmosphere; Schlenk technique;
78%	With hydrogen at 130℃; for 12h;
75%	With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; acetic acid In 1,4-dioxane at 80℃; for 3h;
	Multi-step reaction with 2 steps 1.1: 0.08 h / 70 °C / Microwave irradiation 1.2: 0.08 h / 90 °C / Microwave irradiation 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 - 25 °C
	Multi-step reaction with 2 steps 1: tert-butylbenzene; hydrogen; platinum / 1,4-dioxane / 80 °C / 750.08 Torr / Sealed tube 2: tert-butylbenzene; hydrogen; platinum / 1,4-dioxane / 80 °C / 750.08 Torr / Sealed tube
96 %Chromat.	With aluminum (III) chloride In ethanol at 70℃; for 12h; chemoselective reaction;
	With hydrogen In toluene at 140℃; for 18h;
95 %Chromat.	With hydrogen In methanol at 30℃; for 24h; Autoclave; Green chemistry;
	With tetra(n-butyl)ammonium hydrogensulfate In N,N-dimethyl-formamide at 20℃; for 5h; Electrolysis;

Reference： [1]Mishra, Kanchan; Kim, Sung Hong; Lee, Yong Rok [ChemSusChem, 2019, vol. 12, # 4, p. 881 - 889]
[2]Wang, Shengdong; Huang, Haiyun; Bruneau, Christian; Fischmeister, Cédric [ChemSusChem, 2017, vol. 10, # 21, p. 4150 - 4154]
[3]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525] Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Journal of Organic Chemistry, 2019, vol. 84, # 20, p. 12893 - 12903]
[4]Hoshimoto, Yoichi; Kinoshita, Takuya; Hazra, Sunit; Ohashi, Masato; Ogoshi, Sensuke [Journal of the American Chemical Society, 2018, vol. 140, # 23, p. 7292 - 7300]
[5]Wang, Shengdong; Huang, Haiyun; Bruneau, Christian; Fischmeister, Cédric [Catalysis science and technology, 2019, vol. 9, # 15, p. 4077 - 4082]
[6]Sui, Dejun; Mao, Fei; Fan, Haipeng; Qi, Zhengliang; Huang, Jun [Chinese Journal of Chemistry, 2017, vol. 35, # 9, p. 1371 - 137]
[7]He, Jianghua; Wang, Tianlong; Xu, Hai; Zhang, Yuetao [Tetrahedron, 2020]
[8]Park, Jang Won; Chung, Young Keun [ACS Catalysis, 2015, vol. 5, # 8, p. 4846 - 4850]
[9]Current Patent Assignee: SEOUL NATIONAL UNIVERSITY - KR2016/115061, 2016, A Location in patent: Paragraph 0130-0133
[10]Zhou, Yang; Chen, Ping; Lv, Xue; Niu, Junxing; Wang, Yingying; Lei, Min; Hu, Lihong [Tetrahedron Letters, 2017, vol. 58, # 23, p. 2232 - 2235]
[11]Kumar, Vishal; Sharma, Upendra; Verma, Praveen K.; Kumar, Neeraj; Singh, Bikram [Advanced Synthesis and Catalysis, 2012, vol. 354, # 5, p. 870 - 878]
[12]Kumar, Vishal; Sharma, Upendra; Singh, Bikram; Kumar, Neeraj [Australian Journal of Chemistry, 2012, vol. 65, # 12, p. 1594 - 1598]
[13]Fasano, Valerio; Radcliffe, James E.; Ingleson, Michael J. [ACS Catalysis, 2016, vol. 6, # 3, p. 1793 - 1798]
[14]Tian, Youping; Wei, Junmei; Wang, Meng; Li, Gaoqiang; Xu, Feng [Tetrahedron Letters, 2018, vol. 59, # 19, p. 1866 - 1870]
[15]Ding, Guangni; Wu, Xiaoyu; Jiang, Lili; Zhang, Zhaoguo; Xie, Xiaomin [Organic Letters, 2017, vol. 19, # 22, p. 6048 - 6051]
[16]Raut, Amol B.; Shende, Vaishali S.; Sasaki, Takehiko; Bhanage, Bhalchandra M. [Journal of Catalysis, 2020, vol. 383, p. 206 - 214]
[17]Cao, Hongxuan; Chen, Han; Han, Xinya; Huang, Yunyuan; Liu, Jiaqi; Peng, Chao; Rao, Li; Ren, Yanliang; Sheng, Chunquan; Su, Chen; Tu, Jie; Wan, Chen; Wan, Jian; Wen, Wuqiang [Journal of Medicinal Chemistry, 2022, vol. 65, # 3, p. 2656 - 2674]
[18]Ordonez, Mario; Tibhe, Gaurao D.; Zamudio-Medina, Angel; Viveros-Ceballos, Jose Luis [Synthesis, 2012, vol. 44, # 4, p. 569 - 574]
[19]Shi, Linyan; Hu, Lei; Wang, Jiaqing; Cao, Xueqin; Gu, Hongwei [Organic Letters, 2012, vol. 14, # 7, p. 1876 - 1879]
[20]Kumar, Vishal; Sharma, Sushila; Sharma, Upendra; Singh, Bikram; Kumar, Neeraj [Green Chemistry, 2012, vol. 14, # 12, p. 3410 - 3414]
[21]Mao, Fei; Sui, Dejun; Qi, Zhengliang; Fan, Haipeng; Chen, Rizhi; Huang, Jun [RSC Advances, 2016, vol. 6, # 96, p. 94068 - 94073]
[22]Chaudhari, Chandan; Nagaoka, Katsutoshi; Nishida, Yoshihide; Sato, Katsutoshi; Shiraishi, Masaya [Green Chemistry, 2020, vol. 22, # 22, p. 7760 - 7764]
[23]Zou, Zirong; Cai, Genuo; Chen, Weihao; Zou, Canlin; Li, Yamei; Wu, Hongting; Chen, Lu; Hu, Jinhui; Li, Yibiao; Huang, Yubing [Journal of Organic Chemistry, 2021, vol. 86, # 21, p. 15777 - 15784]

24
[ 1374222-82-8 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; for 0.5h;

Reference： [1]Location in patent: experimental part Ordonez, Mario; Tibhe, Gaurao D.; Zamudio-Medina, Angel; Viveros-Ceballos, Jose Luis [Synthesis, 2012, vol. 44, # 4, p. 569 - 574]

25
[ 28519-62-2 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	With tert-butylbenzene; hydrogen; platinum In 1,4-dioxane at 80℃; Sealed tube;

Reference： [1]Shi, Linyan; Hu, Lei; Wang, Jiaqing; Cao, Xueqin; Gu, Hongwei [Organic Letters, 2012, vol. 14, # 7, p. 1876 - 1879]

26
[ 98-95-3 ]
[ 119-67-5 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
99.5%	With hydrogen; platinum In 1,4-dioxane at 80℃; Sealed tube;
92%	With hydrogen In water at 100℃; for 14h; Autoclave; Inert atmosphere;
90%	With hydrogen In methanol at 20℃; for 6h;

Reference： [1]Location in patent: experimental part Shi, Linyan; Hu, Lei; Wang, Jiaqing; Cao, Xueqin; Gu, Hongwei [Organic Letters, 2012, vol. 14, # 7, p. 1876 - 1879]
[2]Agostini, Giovanni; Calvino, Jose. J.; Corma, Avelino; Gutiérrez-Tarriño, Silvia; Lopes, Christian W.; Oña-Burgos, Pascual; Rojas-Buzo, Sergio [Green Chemistry, 2021, vol. 23, # 12, p. 4490 - 4501]
[3]Cho, Ahra; Byun, Sangmoon; Kim, B. Moon [Advanced Synthesis and Catalysis, 2018, vol. 360, # 6, p. 1253 - 1261]

27
[ 5388-42-1 ]
[ 33513-42-7 ]
[ 1393881-90-7 ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: N-phenylphthalimidine In N,N-dimethyl-formamide at 0 - 80℃; for 6h; Inert atmosphere; Stage #3: With methanol; potassium hydroxide at 20℃; for 1h; Inert atmosphere;	4.3.1. 3-Chloro-2-phenyl-2H-isoindole-1-carbaldehyde 3 POCl3 (1.53 g, 10 mmol) was added dropwise to DMF (0.73 g, 10 mmol) at 0 °C. The mixture was stirred for 30 min at room temperature. After cooling down the solution back to 0 °C, a suspension of 1-phenylisoindolinone 4 (0.7 g, 3.3 mmol) in DMF (2 mL) was added. Subsequently, the reaction mixture was heated at 80 °C for 6 h. Then, after cooling to room temperature, chloroform (10 mL) and ice were added. The organic layer was collected and the chloroform was removed under reduced pressure. Then, KOH (4 M, 5 mL) and MeOH (5 mL) were added to the crude residue, and the mixture was stirred for 1 h at room temperature. The precipitate was filtered, washed with water, and recrystallized from i-PrOH, to give 3 as a light yellow solid (0.58 g, 69%). Mp=98-99 °C. IR (ATR): νCO=1614 cm-11H NMR (acetone-d6): δ=7.36 (t, J=7.8 Hz, 1H, H-5), 7.49 (t, J=7.8 Hz, 1H, H-6), 7.72 (m, 6H, H-4, N-Ph), 8.33 (d, J=7.8 Hz, 1H, H-7), 9.46 (s, 1H, CHO). 13C{1H} NMR (acetone-d6): δ=118.6, 120.5, 122.2, 124.4, 128.2, 128.4, 129.4, 130.2, 135.3, 176.1. UV-vis: λmax (CHCl3): 379 nm (=22,060 L mol-1 cm-1). Fluo (λex=379 nm): λEm=409 nm. MS (DCI/NH3): m/z=256.0 [MH]+. HRMS (DCI/CH4): m/z calcd for C15H11NOCl: 256.0529; found: 256.0529.

Reference： [1]Location in patent: experimental part Baglai, Iaroslav; Maraval, Valérie; Voitenko, Zoia V.; Duhayon, Carine; Volovenko, Yulian M.; Chauvin, Remi [Tetrahedron, 2012, vol. 68, # 34, p. 6908 - 6913]

28
[ 933-88-0 ]
[ 62-53-3 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 - 20 °C 2.1: iodine; potassium carbonate / acetonitrile / 0.17 h / 20 °C / Sealed tube 2.2: 140 °C / Sealed tube
	Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane / 6 h / 0 - 20 °C 2: dmap; copper(l) iodide; di-tert-butyl peroxide / dichloromethane / 24 h / 100 °C / Sealed tube

Reference： [1]Verma, Ajay; Patel, Saket; Meenakshi; Kumar, Amit; Yadav, Abhimanyu; Kumar, Shailesh; Jana, Sadhan; Sharma, Shubham; Prasad, Ch. Durga; Kumar, Sangit [Chemical Communications, 2015, vol. 51, # 7, p. 1371 - 1374]
[2]Nozawa-Kumada, Kanako; Kadokawa, Jun; Kameyama, Takehiro; Kondo, Yoshinori [Organic Letters, 2015, vol. 17, # 18, p. 4479 - 4481]

29
[ 7055-03-0 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 2-methyl-N-phenylbenzamide With iodine; potassium carbonate In acetonitrile at 20℃; for 0.166667h; Sealed tube; Stage #2: With di-tert-butyl peroxide In acetonitrile at 140℃; Sealed tube;
82%	With dmap; copper(l) iodide; di-tert-butyl peroxide In dichloromethane at 100℃; for 24h; Sealed tube;

Reference： [1]Verma, Ajay; Patel, Saket; Meenakshi; Kumar, Amit; Yadav, Abhimanyu; Kumar, Shailesh; Jana, Sadhan; Sharma, Shubham; Prasad, Ch. Durga; Kumar, Sangit [Chemical Communications, 2015, vol. 51, # 7, p. 1371 - 1374]
[2]Nozawa-Kumada, Kanako; Kadokawa, Jun; Kameyama, Takehiro; Kondo, Yoshinori [Organic Letters, 2015, vol. 17, # 18, p. 4479 - 4481]

30
[ 201230-82-2 ]
C₂₀H₁₉NO₃S [ No CAS ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; potassium carbonate In acetonitrile at 140℃; for 21h; Autoclave;	General procedure for the intramolecularcycloaminocarbonylation of 2-aminomethyl(or 2-alkylcarbamoyl)aryl tosylates andcharacterization General procedure: 2-(Aminomethyl)aryl tosylate (2mmol), Pd(OAc)2 (10 mol %), dppp (15 mol %), K2CO3(2.4 mmol) and CH3CN (70 ml) were charged in a 200ml-autoclave. Theautoclave was flushed and then pressurized with carbon monoxide to 1 MPa, themixture was stirred at 140 oC for 21h. The mixture was cooled toroom temperature and vented to discharge the excess CO. After filtration,solvent was removed under reduced pressure and the crude residue was purifiedby column chromatography on silica gel with petroleum ether-ethyl acetate asthe eluent to afford the desired product.

Reference： [1]Liu, Bin; Wang, Yan; Liao, Benren; Zhang, Chunlei; Zhou, Xigeng [Tetrahedron Letters, 2015, vol. 56, # 42, p. 5776 - 5780]

31
[ 131-11-3 ]
[ 62-53-3 ]
[ 19375-67-8 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 60% 2: 25%	With tris(2,4-pentanedionato)ruthenium(III); hydrogen; bis(trifluoromethanesulfonyl)amide; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 150℃; for 18h; Autoclave;

Reference： [1]Adam, Rosa; Cabrero-Antonino, Jose R.; Junge, Kathrin; Jackstell, Ralf; Beller, Matthias [Angewandte Chemie - International Edition, 2016, vol. 55, # 37, p. 11049 - 11053][Angew. Chem., 2016, vol. 128, # 37, p. 11215 - 11219,5]

32
[ 106-47-8 ]
[ 119-67-5 ]
[ 5388-42-1 ]
[ 4775-27-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 70% 2: 20%	With 1,4-diaza-bicyclo[2.2.2]octane; formic acid; palladium diacetate In 1,4-dioxane at 80℃; for 1h;	General procedure for the synthesis of compounds 3 General procedure: A mixture of 2-formylbenzoic acid (1) (2.0 mmol), amine (2) (2.4 mmol, 1.2 equiv), DABCO (448 mg, 2 equiv), HCOOH (0.5 mL), Pd(OAc)2 (22.5 mg, 0.1 mmol, 5 mol%) in 1,4-dioxane (2 mL) was heated to 80 oC for an appropriate time (Table 3). After completion of the reaction, the mixture was cooled to room temperature, and diluted with DCM (20 mL). The solid was removed by filter, and the filtrate was washed with water (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/acetone = 5/1, v/v) to afford the product 3.

Reference： [1]Zhou, Yang; Chen, Ping; Lv, Xue; Niu, Junxing; Wang, Yingying; Lei, Min; Hu, Lihong [Tetrahedron Letters, 2017, vol. 58, # 23, p. 2232 - 2235]

33
[ 4122-56-9 ]
[ 62-53-3 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 1,4-diaza-bicyclo[2.2.2]octane; formic acid; palladium diacetate In 1,4-dioxane at 80℃; for 1h;	General procedure for the synthesis of compounds 3a from methyl 2-formylbenzoate (4) A mixture of methyl 2-formylbenzoate (4) (328 mg, 2.0 mmol), aniline (2a) (223 mg, 2.4 mmol, 1.2 equiv), DABCO (448 mg, 2 equiv), HCOOH (0.5 mL), Pd(OAc)2 (22.5 mg, 0.1 mmol, 5 mol%) in 1,4-dioxane (2 mL) was heated to 80 oC for 1 h. After completion of the reaction, the mixture was cooled to room temperature, and diluted with DCM (20 mL). The solid was removed by filter, and the filtrate was washed with water (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/acetone = 5/1, v/v) to afford the product 3a in 95% yield.

Reference： [1]Zhou, Yang; Chen, Ping; Lv, Xue; Niu, Junxing; Wang, Yingying; Lei, Min; Hu, Lihong [Tetrahedron Letters, 2017, vol. 58, # 23, p. 2232 - 2235]

34
[ 5388-42-1 ]
2-phenyl-3,3-dideuterioisoindolin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: N-phenylphthalimidine With potassium <i>tert</i>-butylate In 1,4-dioxane at 110℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: With water-d2 In 1,4-dioxane Schlenk technique; Inert atmosphere;

Reference： [1]Ding, Guangni; Wu, Xiaoyu; Jiang, Lili; Zhang, Zhaoguo; Xie, Xiaomin [Organic Letters, 2017, vol. 19, # 22, p. 6048 - 6051]

35
[ 480-91-1 ]
[ 591-50-4 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
50%	With copper (I) iodide; Cs₂CO₃; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 20 - 120℃;	General Procedure A for the Synthesis of Compounds A1~A12. General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 μL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 °C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.
48%	With tripotassium phosphate tribasic; copper (I) iodide In dimethyl sulfoxide at 120℃;
	With tripotassium phosphate tribasic; copper (I) iodide In dimethyl sulfoxide at 20 - 110℃; for 24h; Inert atmosphere; Darkness;

With tripotassium phosphate tribasic; copper (I) iodide

Reference： [1]Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong [Molecules, 2019, vol. 24, # 5]
[2]Deng, Zefeng; Fang, Zhang; Huang, Pengcheng; Li, Bao; Shu, Sai; Zhao, Yingsheng; Zhou, Guanyu [European Journal of Organic Chemistry, 2022, vol. 2022, # 14]
[3]Chen, Jiangbo; Wang, Jiaquan; Tu, Tao [Chemistry - An Asian Journal, 2018, vol. 13, # 17, p. 2559 - 2565]
[4]Lai, Huifang; Xu, Jiexin; Lin, Jin; Zha, Daijun [Organic and Biomolecular Chemistry, 2021, vol. 19, # 35, p. 7621 - 7626]

36
[ 5388-42-1 ]
[ 107456-50-8 ]

Yield	Reaction Conditions	Operation in experiment
14 %Spectr.	With potassium phosphate; C₃₀H₃₄BNOPRu; hydrogen In tetrahydrofuran at 150℃; for 24h; Glovebox; Autoclave;

Reference： [1]Chen, Jiangbo; Wang, Jiaquan; Tu, Tao [Chemistry - An Asian Journal, 2018, vol. 13, # 17, p. 2559 - 2565]

37
[ 19375-67-8 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
69%	With sodium azide; oxygen; potassium carbonate; eosin Y disodium salt In dimethyl sulfoxide at 20℃; for 16h; Irradiation; Green chemistry;
59%	With oxygen; potassium carbonate In dimethyl sulfoxide at 20℃; for 24h; Irradiation; Green chemistry;
55%	With 1,4-dioxane at 50℃; for 8h; chemoselective reaction;

42%

With 1,4-diaza-bicyclo[2.2.2]octane; 5-methyl-2-furanone; oxygen In tetrahydrofuran at 25℃; for 36h;

Reference： [1]Aganda, Kim Christopher C.; Hong, Boseok; Lee, Anna [Advanced Synthesis and Catalysis, 2019, vol. 361, # 5, p. 1124 - 1129]
[2]Geng, Pengxin; Tang, Yurong; Pan, Guanglong; Wang, Wentao; Hu, Jinchuan; Cai, Yunfei [Green Chemistry, 2019, vol. 21, # 22, p. 6116 - 6122]
[3]Thapa, Pawan; Corral, Esai; Sardar, Sinjinee; Pierce, Brad S.; Foss, Frank W. [Journal of Organic Chemistry, 2019, vol. 84, # 2, p. 1025 - 1034]
[4]Thatikonda, Thanusha; Deepake, Siddharth K.; Das, Utpal [Organic Letters, 2019, vol. 21, # 8, p. 2532 - 2535]

38
[ 5388-42-1 ]
[ 4778-78-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; ammonium peroxydisulfate In trifluoroacetic acid at 80℃; for 15h; Schlenk technique; Inert atmosphere; regioselective reaction;
	With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; acetic acid; silver carbonate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Dorcet, Vincent; Roisnel, Thierry; Gramage-Doria, Rafael [Journal of Organic Chemistry, 2019, vol. 84, # 4, p. 1898 - 1907]
[2]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525]

39
[ 5388-42-1 ]
2-(2,6-dihydroxyphenyl)isoindolin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; ammonium peroxydisulfate In trifluoroacetic acid at 80℃; for 15h; Schlenk technique; Inert atmosphere; regioselective reaction;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Dorcet, Vincent; Roisnel, Thierry; Gramage-Doria, Rafael [Journal of Organic Chemistry, 2019, vol. 84, # 4, p. 1898 - 1907]

40
[ 83-25-0 ]
[ 5388-42-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With borane-ammonia complex; tris(pentafluorophenyl)borate In 1,2-dichloro-ethane at 60℃; for 16h;

Reference： [1]Pan, Yixiao; Luo, Zhenli; Han, Jiahong; Xu, Xin; Chen, Changjun; Zhao, Haoqiang; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang [Advanced Synthesis and Catalysis, 2019, vol. 361, # 10, p. 2301 - 2308]

41
[ 5388-42-1 ]
[ 74-11-3 ]
2-(1-oxoisoindolin-2-yl)phenyl 4-chlorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; silver carbonate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525]

42
[ 5388-42-1 ]
[ 456-22-4 ]
2-(1-oxoisoindolin-2-yl)phenyl 4-fluorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; silver carbonate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525]

43
[ 5388-42-1 ]
[ 535-80-8 ]
2-(1-oxoisoindolin-2-yl)phenyl 3-chlorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; silver carbonate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525]

44
[ 5388-42-1 ]
[ 586-76-5 ]
2-(1-oxoisoindolin-2-yl)phenyl 4-bromobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; silver carbonate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525]

45
[ 5388-42-1 ]
[ 619-58-9 ]
2-(1-oxoisoindolin-2-yl)phenyl 4-iodobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; silver carbonate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525]

46
[ 5388-42-1 ]
[ 455-24-3 ]
2-(1-oxoisoindolin-2-yl)phenyl 4-(trifluoromethyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; silver carbonate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525]

47
[ 5388-42-1 ]
[ 121-92-6 ]
2-(1-oxoisoindolin-2-yl)phenyl 3-nitrobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; silver carbonate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525]

48
[ 5388-42-1 ]
[ 586-38-9 ]
2-(1-oxoisoindolin-2-yl)phenyl 3-methoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; silver carbonate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525]

49
[ 5388-42-1 ]
[ 445-29-4 ]
2-(1-oxoisoindolin-2-yl)phenyl 2-fluorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; silver carbonate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525]

50
[ 5388-42-1 ]
[ 118-91-2 ]
2-(1-oxoisoindolin-2-yl)phenyl 2-chlorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; silver carbonate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525]

51
[ 5388-42-1 ]
[ 93-09-4 ]
2-(1-oxoisoindolin-2-yl)phenyl 2-naphthoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; silver carbonate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525]

52
[ 527-72-0 ]
[ 5388-42-1 ]
2-(1-oxoisoindolin-2-yl)phenyl thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; silver carbonate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525]

53
[ 88-14-2 ]
[ 5388-42-1 ]
2-(1-oxoisoindolin-2-yl)phenyl furan-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; silver carbonate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525]

54
[ 5388-42-1 ]
[ 292638-85-8 ]
C₁₈H₁₅NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate In 2-methyltetrahydrofuran at 100℃; for 15h; Schlenk technique; Sealed tube; regioselective reaction;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Catalysis science and technology, 2019, vol. 9, # 17, p. 4711 - 4717]

55
[ 5388-42-1 ]
[ 292638-85-8 ]
C₁₈H₁₅NO₃ [ No CAS ]
C₂₂H₁₉NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate In 2-methyltetrahydrofuran at 100℃; for 15h; Schlenk technique; Sealed tube; regioselective reaction;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Catalysis science and technology, 2019, vol. 9, # 17, p. 4711 - 4717]

56
[ 5388-42-1 ]
[ 140-88-5 ]
ethyl (E)-3-(2-(1-oxoisoindolin-2-yl)phenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate In 2-methyltetrahydrofuran at 100℃; for 15h; Schlenk technique; Sealed tube; regioselective reaction;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Catalysis science and technology, 2019, vol. 9, # 17, p. 4711 - 4717]

57
[ 5388-42-1 ]
[ 141-32-2 ]
C₂₁H₂₁NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate In 2-methyltetrahydrofuran at 100℃; for 15h; Schlenk technique; Sealed tube; regioselective reaction;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Catalysis science and technology, 2019, vol. 9, # 17, p. 4711 - 4717]

58
[ 5388-42-1 ]
[ 2495-35-4 ]
C₂₄H₁₉NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate In 2-methyltetrahydrofuran at 100℃; for 15h; Schlenk technique; Sealed tube; regioselective reaction;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Catalysis science and technology, 2019, vol. 9, # 17, p. 4711 - 4717]

59
[ 5388-42-1 ]
[ 107-13-1 ]
C₁₇H₁₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate In 2-methyltetrahydrofuran at 100℃; for 15h; Schlenk technique; Sealed tube; regioselective reaction;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Catalysis science and technology, 2019, vol. 9, # 17, p. 4711 - 4717]

60
[ 5388-42-1 ]
[ 107-02-8 ]
C₁₇H₁₃NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate In 2-methyltetrahydrofuran at 100℃; for 15h; Schlenk technique; Sealed tube; regioselective reaction;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Catalysis science and technology, 2019, vol. 9, # 17, p. 4711 - 4717]

61
[ 5388-42-1 ]
[ 78-94-4 ]
C₁₈H₁₅NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate In 2-methyltetrahydrofuran at 100℃; for 15h; Schlenk technique; Sealed tube; regioselective reaction;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Catalysis science and technology, 2019, vol. 9, # 17, p. 4711 - 4717]

62
[ 100-42-5 ]
[ 5388-42-1 ]
C₂₂H₁₇NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate In 2-methyltetrahydrofuran at 100℃; for 15h; Schlenk technique; Sealed tube; regioselective reaction;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Catalysis science and technology, 2019, vol. 9, # 17, p. 4711 - 4717]

63
[ 5388-42-1 ]
[ 405-99-2 ]
C₂₂H₁₆FNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate In 2-methyltetrahydrofuran at 100℃; for 15h; Schlenk technique; Sealed tube; regioselective reaction;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Catalysis science and technology, 2019, vol. 9, # 17, p. 4711 - 4717]

64
[ 5388-42-1 ]
[ 2039-82-9 ]
C₂₂H₁₆BrNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate In 2-methyltetrahydrofuran at 100℃; for 15h; Schlenk technique; Sealed tube; regioselective reaction;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Catalysis science and technology, 2019, vol. 9, # 17, p. 4711 - 4717]

65
silver hexafluoroantimonate [ No CAS ]
[ 100928-22-1 ]
[ 5388-42-1 ]
C₂₄H₂₅NORu⁽²⁺⁾*2F₆Sb^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In tetrahydrofuran at 55℃;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Catalysis science and technology, 2019, vol. 9, # 17, p. 4711 - 4717]

66
[ 5388-42-1 ]
[ 2216-94-6 ]
C₂₅H₂₁NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) acetate monohydrate In 2-methyltetrahydrofuran at 100℃; for 15h; Schlenk technique; Sealed tube; regioselective reaction;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Catalysis science and technology, 2019, vol. 9, # 17, p. 4711 - 4717]

67
[ 5388-42-1 ]
[ 98-80-6 ]
[ 57877-22-2 ]