1817-49-8|1,3-Diphenylprop-2-yn-1-ol| Ambeed

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1
[ 1817-49-8 ]
[ 614-47-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With triazole-Au In methanol; water at 60℃; for 3h; diastereoselective reaction;
87%	With TriaAu(III)Cl<SUB>2</SUB> In methanol; water at 60℃; for 6h;	1.2 Representative procedure for thepreparation of α,β-unsatured ketone 3a General procedure: To a solution of 2a (0.5 mmol) in wet MeOH (10% H2O) (3 mL), was added TriaAu(III)Cl2 catalyst (1.0 mol%) at RT. The reaction mixture was stirred at 60 oC and monitored by TLC. After the reaction was completed (6 h), the solvent was removed under reduced pressure and purification of the crude product by column chromatography on silica-gel (petroleum ether/ethyl acetate = 20:1) afforded the title compound 3a in 89% yield as a colorless oil.
85%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 80℃; for 18h; Sealed tube;	Chalcones 2a-u; General Procedure General procedure: DBU (10 mol%) was added to a solution of the appropriate propargylicalcohol 1 (1.0 equiv) in dry MeCN (0.2 M) in a sealedtube, and the solution was mixed well by manual shaking. N2gas was flashed into the tube, and the cap was quickly closed.The sealed tube was placed in an oil bath at 80 °C, and themixture was stirred for 18 h until the substrate was completelyconsumed (TLC). The mixture was then allowed to cool to r.t.and the reaction was quenched with H2O (10 mL). The productwas extracted with Et2O (3 × 20 mL), and the combined organiclayers were washed with brine (10 mL), dried (Na2SO4), andconcentrated under reduced pressure. The crude product waspurified by column chromatography [silica gel (100-200 mesh),PE-EtOAc (10:1)].(2E)-1,3-Diphenylprop-2-en-1-one (2a)White solid; yield: 43.2 mg (86%); mp 54-56 °C. IR (ATR): 3059(=CH), 1658 (C=O), 1598 (C=C) cm-1. 1H NMR (400 MHz, CDCl3): =8.02 (d, J = 8.0 Hz, 2 H), 7.81 (d, J = 16.0 Hz, 1 H), 7.63 (dd, J =8.0, 4.0 Hz, 2 H), 7.59-7.48 (m, 4 H), 7.42-7.40 (m, 3 H). 13CNMR (100 MHz, CDCl3): = 190.6, 144.9, 138.2, 134.9, 132.9,130.6, 129.0, 128.7, 128.6, 128.5, 122.2.

80%	With potassium carbonate In acetonitrile at 100℃; for 24h; Sealed tube;	1 Preparation of 1,3-Diphenylprop-2-yn-1-ol (E)-Chalcone Add 1,3-diphenylprop-2-yn-1-ol (2mmol), K2CO3(0.2 equivalent), and acetonitrile (1mL) to a10mL reaction tube. The reaction mixture is directly sealed under air and heated to React at 100°C for 24h.The E/Z=99/1 of the product was detected by GC-MS.After the solvent was evaporated from the reaction mixture, column chromatography was separated and purified to obtain (E)-chalcone with a separation yield of 80%.
70%	With potassium hydroxide In toluene at 80℃; for 1h;
	With dimethyl sulfoxide; triethylamine at 140℃;
	Multi-step reaction with 2 steps 1: 2.05 g / 4-dimethylaminopyridine; Et₃N 2: 92 percent / water / silver hexafluoroantimonate; (ItBu)AuCl / tetrahydrofuran / 8 h / 60 °C
	Multi-step reaction with 3 steps 1: 98 percent / triethylamine / tetrahydrofuran / 0.5 h / 0 - 20 °C 2: t-BuOK / tetrahydrofuran / 0.17 h / -78 °C 3: aq. sulfuric acid / tetrahydrofuran; 1,2-dimethoxy-ethane / 0.17 h / -78 °C
	With [ReOCl₃(OPPh₃)(SMe₂)]; water In 1,2-dimethoxyethane; hexane at 80℃; for 24h; Inert atmosphere; stereoselective reaction;
	Multi-step reaction with 2 steps 1: manganese(IV) oxide / dichloromethane / 2 h / 20 °C / Darkness; Schlenk technique 2: triphenylphosphine; benzoic acid; water / tetrahydrofuran / 24 h / 65 °C
59 %Chromat.	With Mg₃Al-CO₃-layered double hydroxide In toluene at 100℃; for 0.166667h; Inert atmosphere;

Reference： [1]Wang, Dawei; Zhang, Yanwei; Harris, Alexandria; Gautam, Lekh Nath S.; Chen, Yunfeng; Shi, Xiaodong [Advanced Synthesis and Catalysis, 2011, vol. 353, # 14-15, p. 2584 - 2588]
[2]Yang, Yongchun; Shen, Yanan; Wang, Xiaoli; Zhang, Yao; Wang, Dawei; Shi, Xiaodong [Tetrahedron Letters, 2016, vol. 57, # 21, p. 2280 - 2282]
[3]De, Rimpa; Savarimuthu, Antony; Ballav, Tamal; Singh, Pijush; Nanda, Jayanta; Hasija, Avantika; Chopra, Deepak; Bera, Mrinal K. [Synlett, 2020, vol. 31, # 16, p. 1587 - 1592]
[4]Current Patent Assignee: WENZHOU UNIVERSITY - CN113461501, 2021, A Location in patent: Paragraph 0027-0030
[5]Cho, Chan Sik; Lee, Na Young; Kim, Tae-Jeong; Shim, Sang Chul [Journal of Heterocyclic Chemistry, 2004, vol. 41, # 3, p. 409 - 411]
[6]Migliorese,K.G. et al. [Journal of Organic Chemistry, 1974, vol. 39, p. 739 - 747]
[7]Marion, Nicolas; Carlqvist, Peter; Gealageas, Ronan; De Fremont, Pierre; Maseras, Feliu; Nolan, Steven P. [Chemistry - A European Journal, 2007, vol. 13, # 22, p. 6437 - 6451]
[8]Yoshizawa, Kazuhiro; Shioiri, Takayuki [Tetrahedron, 2007, vol. 63, # 27, p. 6259 - 6286]
[9]Mattia, Elio; Porta, Alessio; Merlini, Valentina; Zanoni, Giuseppe; Vidari, Giovanni [Chemistry - A European Journal, 2012, vol. 18, # 38, p. 11894 - 11898]
[10]Pierce, Brett M.; Simpson, Brittany F.; Ferguson, Kane H.; Whittaker, Rachel E. [Organic and Biomolecular Chemistry, 2018, vol. 16, # 36, p. 6659 - 6662]
[11]Yatabe, Takafumi; Mizuno, Noritaka; Yamaguchi, Kazuya [ACS Catalysis, 2018, vol. 8, # 12, p. 11564 - 11569]

2
[ 591-50-4 ]
[ 4187-87-5 ]
[ 1817-49-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In tetrahydrofuran Heating;
96%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 2h;
94%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 20℃; for 24h;	1,3-Diphenylprop-2-yn-1-ol To a stirred solution of iodobenzene (612 mg, 3 mmol), in a component solvent of diisopropylamine (5 mL) and THF (5 mL), CuI (30 mg, 5 mol%) and (PPh3)2PdCl2 (105 mg, 5 mol%) were added. A solution of 1-phenylprop-2-yn-1-ol (396 mg, 3 mmol) in THF (2 mL) was added dropwise at room temperature. The reaction mixture was allowed to stir at room temperature for 24 h. The solvent was evaporated and the column chromatography of the crude product afforded 2v as a yellow viscous oil; yield: 587 mg (94%).

83%	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 2h; Sealed tube;
80%	With piperidine; copper(l) iodide; triphenylphosphine In tetrahydrofuran at 100℃; for 0.5h; microwave irradiation;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine 1.) RT, 0.5 h, 2.) RT, 48 h; Yield given. Multistep reaction;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine Inert atmosphere; Sealed flask; Heating;	General Procedure for the Palladium-Catalyzed Formation of Compounds 1: General procedure: 2-methyl-4-phenylbut-3-yn-2-ol (1a): Into a dry Et3N solution (5 ml) containing iodobenzene (5.0 mmol), 2-methylbut-3-yn-2-ol (6.0 mmol) and triphenylphosphine (4 mol %), CuI (5 mol %) was added and the reaction mixture was stirred for 2 min. After the solution was purged with nitrogen for half an hour, PdCl2(PPh3)2 (0.5 mol %) was added and the flask was flushed with N2, sealed and allowed to stir at 50°C for 4 h. The resulting reaction mixture was concentrated under vacuum The residue was purified through column chromatography (silica gel, hexane/ethyl acetate as eluent) to afford a yellow oil.
	With copper(l) iodide; palladium diacetate; triethylamine; triphenylphosphine at 20℃; Inert atmosphere;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran Inert atmosphere;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
	With copper(l) iodide; palladium diacetate; triethylamine; triphenylphosphine In acetonitrile at 20℃; Inert atmosphere;

Reference： [1]Mueller, Thomas J.J.; Ansorge, Markus; Aktah, Daniel [Angewandte Chemie - International Edition, 2000, vol. 39, # 7, p. 1253 - 1256]
[2]Yoshida, Masahiro; Higuchi, Mariko; Shishido, Kozo [Organic Letters, 2009, vol. 11, # 20, p. 4752 - 4755]
[3]Huang, Huawen; Jiang, Huanfeng; Cao, Hua; Zhao, Jinwu; Shi, Dabin [Tetrahedron, 2012, vol. 68, # 14, p. 3135 - 3144]
[4]Díaz-Marta, Antonio S.; Yañez, Susana; Lasorsa, Eliana; Pacheco, Patricia; Tubío, Carmen R.; Rivas, José; Piñeiro, Yolanda; Gómez, Manuel A. Gonzalez; Amorín, Manuel; Guitián, Francisco; Coelho, Alberto [ChemCatChem, 2020, vol. 12, # 6, p. 1762 - 1771]
[5]Schramm, Oana G.; Mueller, Thomas J. J. [Advanced Synthesis and Catalysis, 2006, vol. 348, # 18, p. 2565 - 2570]
[6]Kundu, Nitya G.; Pal, Manojit; Chowdhury, Chinmay [Journal of Chemical Research, Miniprint, 1995, # 1, p. 101 - 123]
[7]Location in patent: scheme or table Nandakumar, Avanashiappan; Balakrishnan, Krishnamoorthy; Perumal, Paramasivan Thirumalai [Synlett, 2011, # 18, p. 2733 - 2739]
[8]Zhou, Chao; Chen, Xiaopeng; Lu, Ping; Wang, Yanguang [Tetrahedron, 2012, vol. 68, # 13, p. 2844 - 2850]
[9]Okamoto, Noriko; Sueda, Takuya; Minami, Hideki; Miwa, Yoshihisa; Yanada, Reiko [Organic Letters, 2015, vol. 17, # 5, p. 1336 - 1339]
[10]Shen, Ruwei; Yang, Jianjun; Zhu, Shugao; Chen, Chao; Wu, Luling [Advanced Synthesis and Catalysis, 2015, vol. 357, # 6, p. 1259 - 1269]
[11]Ambrogio, Ilaria; Cacchi, Sandro; Fabrizi, Giancarlo; Goggiamani, Antonella; Iazzetti, Antonia [European Journal of Organic Chemistry, 2015, vol. 2015, # 14, p. 3147 - 3151]
[12]Cheng, Xing; Yu, Yinghua; Mao, Zhifeng; Chen, Jianxin; Huang, Xueliang [Organic and Biomolecular Chemistry, 2016, vol. 14, # 16, p. 3878 - 3882]
[13]Huang, Bin; Liffert, Raphael; Linden, Anthony; Gademann, Karl [Chemistry - A European Journal, 2019, vol. 25, # 4, p. 981 - 984]

3
[ 93-04-9 ]
[ 1817-49-8 ]
1-(1,3-diphenylprop-2-ynyl)-2-methoxynaphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In 1,2-dichloro-ethane at 60℃; for 1h;
90%	With iron(III) chloride In acetonitrile at 20℃; for 0.5h;
90%	With bismuth(III) chloride In acetonitrile at 35℃; for 0.5h;

Reference： [1]Nishibayashi, Yoshiaki; Inada, Youichi; Yoshikawa, Masato; Hidai, Masanobu; Uemura, Sakae [Angewandte Chemie - International Edition, 2003, vol. 42, # 13, p. 1495 - 1498]
[2]Zhan, Zhuang-Ping; Yu, Jing-Liang; Liu, Hui-Juan; Cui, Yuan-Yuan; Yang, Rui-Feng; Yang, Wen-Zhen; Li, Jun-Ping [Journal of Organic Chemistry, 2006, vol. 71, # 21, p. 8298 - 8301]
[3]Zhan, Zhuang-Ping; Yang, Wen-Zhen; Yang, Rui-Feng; Yu, Jing-Liang; Li, Jun-Ping; Liu, Hui-Juan [Chemical Communications, 2006, # 31, p. 3352 - 3354]

4
[ 1817-49-8 ]
[ 79257-61-7 ]
<i>N</i>-[2-(1,3-diphenyl-prop-2-ynyl)-3,5-dimethoxy-phenyl]-acetamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2003,vol. 42,p. 1495 - 1498

5
[ 1817-49-8 ]
[ 151-10-0 ]
1-[3-(2,4-dimethoxyphenyl)-3-phenylprop-1-ynyl]benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With boron trifluoride diethyl etherate In acetonitrile at 0℃; for 0.0833333h;
91%	In 1,2-dichloro-ethane at 60℃; for 3h;
91%	With scandium tris(trifluoromethanesulfonate) at 20 - 60℃; for 5.25h; Inert atmosphere; Ionic liquid; regioselective reaction;

83%	With potassium hexafluorophosphate In nitromethane for 5h; Heating;
83%	With calcium(II) bis(trifluoromethanesulfonyl)imide; tert-butylammonium hexafluorophosphate(V) In dichloromethane at 20℃; for 2h; regioselective reaction;

Reference： [1]Liu, Jianhui; Muth, Enrico; Floerke, Ulrich; Henkel, Gerald; Merz, Klaus; Sauvageau, Janelle; Schwake, Erik; Dyker, Gerald [Advanced Synthesis and Catalysis, 2006, vol. 348, # 4-5, p. 456 - 462]
[2]Nishibayashi, Yoshiaki; Inada, Youichi; Yoshikawa, Masato; Hidai, Masanobu; Uemura, Sakae [Angewandte Chemie - International Edition, 2003, vol. 42, # 13, p. 1495 - 1498]
[3]Location in patent: experimental part Aridoss, Gopalakrishnan; Sarca, Viorel D.; Ponder Jr, James F.; Crowe, Jessica; Laali, Kenneth K. [Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2518 - 2529]
[4]Kennedy-Smith, Joshua J.; Young, Lauren A.; Toste, F. Dean [Organic Letters, 2004, vol. 6, # 8, p. 1325 - 1327]
[5]Niggemann, Meike; Meel, Matthias J. [Angewandte Chemie - International Edition, 2010, vol. 49, # 21, p. 3684 - 3687]

6
[ 1817-49-8 ]
[ 275-51-4 ]
(1,3-diphenylpropyn-3-yl)-azulene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	In 1,2-dichloro-ethane at 60℃; for 25h;
54%	With boron trifluoride diethyl etherate In acetonitrile at 0℃; for 0.0833333h;

Reference： [1]Nishibayashi, Yoshiaki; Inada, Youichi; Yoshikawa, Masato; Hidai, Masanobu; Uemura, Sakae [Angewandte Chemie - International Edition, 2003, vol. 42, # 13, p. 1495 - 1498]
[2]Liu, Jianhui; Muth, Enrico; Floerke, Ulrich; Henkel, Gerald; Merz, Klaus; Sauvageau, Janelle; Schwake, Erik; Dyker, Gerald [Advanced Synthesis and Catalysis, 2006, vol. 348, # 4-5, p. 456 - 462]

7
[ 634-36-6 ]
[ 1817-49-8 ]
1-(1,3-diphenyl-2-propynyl)-2,3,4-trimethoxybenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium hexafluorophosphate In nitromethane Heating;
89%	With tin(ll) chloride In nitromethane at 40℃; for 0.166667h;

Reference： [1]Kennedy-Smith, Joshua J.; Young, Lauren A.; Toste, F. Dean [Organic Letters, 2004, vol. 6, # 8, p. 1325 - 1327]
[2]Masuyama, Yoshiro; Hayashi, Miki; Suzuki, Noriyuki [European Journal of Organic Chemistry, 2013, # 14, p. 2914 - 2921]

8
[ 98-10-2 ]
[ 1817-49-8 ]
1-[1-(phenylsulfonamido)-3-phenyl-2-propynyl]benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With aluminium(III) triflate In acetonitrile at 60℃; for 6.5h;	General procedure: Al(OTf)3 (0.5 mol %) was added to the propargyl alcohol (1 mmol) and the nucleophile (1 mmol, 1 equiv) in CH3CN (2.5 mL) and the mixture heated to 60 °C for the time indicated in Table 1. After completion of the reaction (TLC), the solvent was removed under reduced pressure, and the residue purified by column chromatography on silica gel (EtOAc:hexane 5:95, v/v) to afford the pure product. The physical data of known compounds were identical to those published (see references in Table 1).
86%	With molybdenum(V) chloride In dichloromethane at 20℃; for 10h;
80%	With phosphomolybdic acid on silica In 1,2-dichloro-ethane at 20℃; for 7h;

67%

With pyridinium p-toluenesulfonate In acetonitrile at 80℃; for 1h;

Reference： [1]Location in patent: experimental part Gohain, Mukut; Marais, Charlene; Bezuidenhoudt, Barend C.B. [Tetrahedron Letters, 2012, vol. 53, # 9, p. 1048 - 1050]
[2]Reddy, Ch. Raji; Madhavi, P. Phani; Reddy, A. Syamprasad [Tetrahedron Letters, 2007, vol. 48, # 40, p. 7169 - 7172]
[3]Yadav; Reddy, B. V. Subba; Rao, T. Srinivasa; Bala; Krishna; Kumar, G. G. K. S. Narayana [Chemistry Letters, 2007, vol. 36, # 12, p. 1472 - 1473]
[4]Sanz, Roberto; Martinez, Alberto; Alvarez-Gutierrez, Julia M.; Rodriguez, Felix [European Journal of Organic Chemistry, 2006, # 6, p. 1383 - 1386]

9
[ 874-23-7 ]
[ 1817-49-8 ]
2-acetyl-2-(1,3-diphenyl-2-propynyl)cyclohexanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With bismuth (III) nitrate pentahydrate; 3-butyl-1-ethyl-4-nitroimidazolium bis(trifluoromethylsulfonyl)imide; at 20 - 40℃; for 3.16667h;Inert atmosphere;	General procedure: The desired ionic liquid (2 mL if the reactants were liquids and 3.00-3.5 mL for solids) was charged into an oven-dried Schlenk tube under a nitrogen atmosphere, The Lewis acid (10 mol%) was then introduced and was dissolved or immobilized in the IL upon sonication (for about 15 min). No catalyst was used in entries 1 and 9 in Table 1. The respective 1,3-diketone or the 4-hydroxycoumarin was then introduced into the Schlenk tube under a nitrogen atmosphere followed by the desired propargylic alcohol. The reaction mixture was magnetically stirred, initially at r. t. for about 10 minutes followed by stirring in a pre-heated oil bath at 30 to 60 C (as specified; refer to Tables 1-3), until completion (monitored by TLC). Once the reaction was over, the contents were cooled to r. t. and extracted with dry diethyl ether or with EtOAc-Hexane (2:3 vol/vol), until the final extraction did not show a spot corresponding to the starting material or to the product). The combined organic extracts were washed with DI water, dried with MgSO4 and concentrated to give the crude product, which upon purification through column chromatography furnished the desired products. In some cases the crude reaction mixture obtained upon evaporation of the combined organic extracts was directly charged onto a column for purification without a water wash.

Reference： [1]Synthetic Communications,2011,vol. 41,p. 243 - 254
[2]Chemistry Letters,2008,vol. 37,p. 878 - 879
[3]Tetrahedron Letters,2011,vol. 52,p. 6859 - 6864
[4]Organic Letters,2007,vol. 9,p. 727 - 730

10
[ 1817-49-8 ]
[ 120-46-7 ]
2-(1,3-diphenyl-2-propynyl)-1,3-diphenylpropane-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In nitromethane at 20℃; for 0.5h;
94%	In dichloromethane at 0℃; for 1h;
94%	With iron(III) chloride In dichloromethane at 20℃; for 2h;

93%	With toluene-4-sulfonic acid In acetonitrile for 1h; Heating;
92%	With lanthanum(III) nitrate hexahydrate In neat (no solvent) at 90℃; for 0.5h; Green chemistry;	General procedure: A mixture of 1,3-dicarbonyl compound 1 (0.75 mmol), alcohol 2 (0.50 mmol) and La(NO3)3*6H2O (5 mg) was allowed to heat at 90 °C for the indicated time (Table-2). After completion of the reaction as noticed by TLC, the reaction mixture was cooled to room temperature and diluted with water (5 mL) and extracted into ethyl acetate (2 x 10 mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to get crude product, which was purified on silica gel column chromotography using hexane and ethyl acetate as eluent to give pure product 3.
91%	With bismuth (III) nitrate pentahydrate; 3-butyl-1-ethyl-4-nitroimidazolium bis(trifluoromethylsulfonyl)imide at 20 - 30℃; for 2.16667h; Inert atmosphere;	General procedure for propargylation of diketones and 4-hydroxycoumarins: General procedure: The desired ionic liquid (2 mL if the reactants were liquids and 3.00-3.5 mL for solids) was charged into an oven-dried Schlenk tube under a nitrogen atmosphere, The Lewis acid (10 mol%) was then introduced and was dissolved or immobilized in the IL upon sonication (for about 15 min). No catalyst was used in entries 1 and 9 in Table 1. The respective 1,3-diketone or the 4-hydroxycoumarin was then introduced into the Schlenk tube under a nitrogen atmosphere followed by the desired propargylic alcohol. The reaction mixture was magnetically stirred, initially at r. t. for about 10 minutes followed by stirring in a pre-heated oil bath at 30 to 60 °C (as specified; refer to Tables 1-3), until completion (monitored by TLC). Once the reaction was over, the contents were cooled to r. t. and extracted with dry diethyl ether or with EtOAc-Hexane (2:3 vol/vol), until the final extraction did not show a spot corresponding to the starting material or to the product). The combined organic extracts were washed with DI water, dried with MgSO4 and concentrated to give the crude product, which upon purification through column chromatography furnished the desired products. In some cases the crude reaction mixture obtained upon evaporation of the combined organic extracts was directly charged onto a column for purification without a water wash.
89%	With indium(III) bromide In 1,2-dichloro-ethane at 80℃; for 5h;
88%	In 1,2-dichloro-ethane at 20℃; for 2.5h;
86%	With sulfuric acid In nitromethane at 101℃; for 0.0833333h;	Typical procedure A for the reaction of β-dicarbonyl compound with alcohol catalyzed by H₂SO₄ under conventional heating condition General procedure: β-Dicarbonyl compound (3.0 mmol) and alcohol (1.0 mmol) were combined in 2 mL of nitromethane, and H2SO4 (2.7 μL, 0.05 mmol) was added. The mixture was stirred under 101 oC in oil bath for 5 min. Then Na2CO3 (10 mg) was added to the reaction mixture to quench the reaction and the solvent was removed under reduced pressure, and the residue was flash column chromatographed over silica gel to afford the product.
75%	With tin(ll) chloride In nitromethane at 40℃; for 0.166667h;
52%	With tetrafluoroboric acid In nitromethane; water for 0.0833333h; Microwave irradiation;
	With silver hexafluoroantimonate In toluene at 60℃;	1 4.2 General procedure for the synthesis of fully substituted pyrroles General procedure: To a stirred solution of propargylic alcohol (1a-k, 0.5 mmol) in toluene (2 mL) were added 1,3-dicarbonyl compound (2a-c, 0.55 mmol) and AgSbF6 (0.025 mmol, purchased from Sigma-Aldrich Co.) and the mixture was heated at 60 °C. After consumption of the starting materials, an appropriate amine (0.55 mmol) was added and the reaction continued at the same temperature until completion (GC and TLC analysis). When an aliphatic amine (3g-n) was used, 0.55 mmol HOAc was added prior to the addition of amine. The reaction mixture was diluted with ethyl acetate (10 mL), and then washed with water (5 mL) and brine (5 mL). The organic layer was dried over anhydrous MgSO4, filtered, and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (EtOAc/hexanes) to give desired products.
	With silver hexafluoroantimonate In toluene at 90℃;	General procedure: To a stirred solution of propargylic alcohol (1, 0.5 mmol) in toluene (2 mL) were added 1,3-dicarbonyl compound (2,0.55 mmol) and AgSbF6(0.025 mmol), and the mixture was heated at 90C.

Reference： [1]Huang, Wen; Wang, Jialiang; Shen, Quansheng; Zhou, Xigeng [Tetrahedron, 2007, vol. 63, # 47, p. 11636 - 11643]
[2]Kuninobu, Yoichiro; Ueda, Hirokazu; Takai, Kazuhiko [Chemistry Letters, 2008, vol. 37, # 8, p. 878 - 879]
[3]Location in patent: scheme or table Maiti, Sukhendu; Biswas, Srijit; Jana, Umasish [Synthetic Communications, 2011, vol. 41, # 2, p. 243 - 254]
[4]Sanz, Roberto; Miguel, Delia; Martinez, Alberto; Alvarez-Gutierrez, Julia M.; Rodriguez, Felix [Organic Letters, 2007, vol. 9, # 4, p. 727 - 730]
[5]Subramanyam, Madala; Rao, Koya Prabhakara; Varala, Ravi; Rao, Mandava V. Basaveswara [Asian Journal of Chemistry, 2016, vol. 28, # 5, p. 1155 - 1160]
[6]Aridoss, Gopalakrishnan; Laali, Kenneth K. [Tetrahedron Letters, 2011, vol. 52, # 51, p. 6859 - 6864]
[7]Location in patent: experimental part Yadav; Subba Reddy; Raghavendra Rao; Narender [Tetrahedron Letters, 2009, vol. 50, # 27, p. 3963 - 3965]
[8]Yadav; Subba Reddy; Pandurangam; Raghavendra Rao; Praneeth; Narayana Kumar; Madavi; Kunwar [Tetrahedron Letters, 2008, vol. 49, # 27, p. 4296 - 4301]
[9]Xia, Fei; Zhao, Zheng Le; Liu, Pei Nian [Tetrahedron Letters, 2012, vol. 53, # 23, p. 2828 - 2832]
[10]Masuyama, Yoshiro; Hayashi, Miki; Suzuki, Noriyuki [European Journal of Organic Chemistry, 2013, # 14, p. 2914 - 2921]
[11]Location in patent: experimental part Liu, Peinian; Xia, Fei; Ren, Yujie; Chen, Junqin [Chinese Journal of Chemistry, 2011, vol. 29, # 10, p. 2075 - 2080]
[12]Gujarathi, Satheesh; Liu, Xingui; Song, Lin; Hendrickson, Howard; Zheng, Guangrong [Tetrahedron, 2014, vol. 70, # 34, p. 5267 - 5273]
[13]Gujarathi, Satheesh; Zheng, Guangrong [Tetrahedron, 2015, vol. 71, # 36, p. 6183 - 6188]

11
[ 1817-49-8 ]
[ 2170-06-1 ]
penta-1,4-diyne-1,3,5-triyltribenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With iodine In dichloromethane at 20℃; for 3h;
93%	With iron(III) chloride In nitromethane at 25℃; for 0.0833333h;
89%	With acid-treated K₁₀ montmorillonite at 40℃; for 0.416667h; Neat (no solvent);

76%

In dichloromethane at 25℃; for 3h;

Reference： [1]Yadav; Reddy, B.V. Subba; Thrimurtulu; Reddy, N. Mallikarjuna; Prasad [Tetrahedron Letters, 2008, vol. 49, # 12, p. 2031 - 2033]
[2]Min, Lin; Xin-Liang, Chen; Tao, Wang; Ping, Yan; Su-Xia, Xu; Zhuang-Ping, Zhan [Chemistry Letters, 2011, vol. 40, # 1, p. 111 - 113]
[3]Wang, Tao; Ma, Rui-Da; Liu, Liu; Zhan, Zhuang-Ping [Green Chemistry, 2010, vol. 12, # 9, p. 1576 - 1579]
[4]Kuninobu, Yoichiro; Ishii, Eri; Takai, Kazuhiko [Angewandte Chemie - International Edition, 2007, vol. 46, # 18, p. 3296 - 3299]

12
[ 95-20-5 ]
[ 1817-49-8 ]
3-(1,3-diphenylprop-2-ynyl)-2-methyl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In dichloromethane at 80℃; for 0.5h;
85%	With aluminium(III) triflate In acetonitrile at 85℃; for 2h;	General reaction procedure: General procedure: Al(OTf)3 (2 mol %) was added to a solution of the indole 1 (1 mmol) and alkynol 2 (1.15 mmol, 1.15 equiv) in CH3CN (2.00 ml) and the reaction mixture was refluxed with stirring for the time indicated in Table 2. After completion of the reaction (monitored by GC-MS), the solvent was removed in vacuo and the residue purified by column chromatography on silica gel (EtOAc:hexane 5:95, v/v). All obtained products were fully characterized by spectroscopic analysis (1H NMR, 13C NMR and MS). The physical data of known compounds were identical to those published (see references in Table 2).
81%	With bismuth (III) nitrate pentahydrate at 45℃; for 4h; Ionic liquid; Inert atmosphere;	General procedure for propargylation of indoles and carbazole: General procedure: The ionic liquid (3.5-4.0 mL) was charged into an oven-dried Schlenk tube under a nitrogen atmosphere and Bi(NO3)3·5H2O (10 mol %) was added and upon sonication (for about 15 min) was dissolved in the IL. The respective indoles (1 mmol) or carbazole (1 mmol) was then introduced into the Schlenk tube under a nitrogen atmosphere followed by the desired propargylic alcohol (1 mmol). The reaction mixture was magnetically stirred, initially at rt for about 10 min followed by stirring in a pre-heated oil bath at 35-60 °C (as specified; refer to Tables 1), until completion (as monitored by TLC). Once the reaction was over, the contents were cooled to rt and extracted with dry diethyl ether or with EtOAc/Hexane (2:3 vol/vol in the case of 5-nitro and 5-cyano indole derivatives), until the final extraction did not show a spot corresponding to the starting material or to the product. The combined organic extracts were washed with DI water, dried with MgSO4, and concentrated to give the crude product, which upon purification through column chromatography furnished the desired products.

33%

With iodine In acetonitrile at 20℃; for 20h;

Reference： [1]Yadav; Reddy, B.V. Subba; Rao, K.V. Raghavendra; Kumar, G.G.K.S. Narayana [Tetrahedron Letters, 2007, vol. 48, # 31, p. 5573 - 5576]
[2]Location in patent: experimental part Gohain, Mukut; Marais, Charlene; Bezuidenhoudt, Barend C.B. [Tetrahedron Letters, 2012, vol. 53, # 35, p. 4704 - 4707]
[3]Kumar, G.G.K.S. Narayana; Aridoss, Gopalakrishnan; Laali, Kenneth K. [Tetrahedron Letters, 2012, vol. 53, # 24, p. 3066 - 3069]
[4]Location in patent: experimental part Liu, Zhe; Wang, Dong; Chen, Yongjun [Letters in Organic Chemistry, 2011, vol. 8, # 1, p. 73 - 80]

13
[ 1817-49-8 ]
[ 815-57-6 ]
3-(1,3-diphenyl-2-propynyl)-3-methylpentane-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In nitromethane at 20℃; for 0.5h;
90%	With iron(III) chloride In dichloromethane at 20℃; for 2h;
83%	In dichloromethane at 0℃; for 1h;

60%

With [Pd(1,5-cyclooctadiene)Cl(SnCl₃)] In nitromethane at 85℃; for 6h; regioselective reaction;

Reference： [1]Huang, Wen; Wang, Jialiang; Shen, Quansheng; Zhou, Xigeng [Tetrahedron, 2007, vol. 63, # 47, p. 11636 - 11643]
[2]Location in patent: experimental part Maiti, Sukhendu; Biswas, Srijit; Jana, Umasish [Synthetic Communications, 2011, vol. 41, # 2, p. 243 - 254]
[3]Kuninobu, Yoichiro; Ueda, Hirokazu; Takai, Kazuhiko [Chemistry Letters, 2008, vol. 37, # 8, p. 878 - 879]
[4]Location in patent: experimental part Das, Debjit; Pratihar, Sanjay; Roy, Ujjal Kanti; Mal, Dipakranjan; Roy, Sujit [Organic and Biomolecular Chemistry, 2012, vol. 10, # 23, p. 4537 - 4542]

14
[ 1817-49-8 ]
[ 3274-56-4 ]

Reference： [1]Australian Journal of Chemistry,1992,vol. 45,p. 1167 - 1178

15
[ 948-65-2 ]
[ 1817-49-8 ]
[ 1000703-54-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With indium(III) bromide In 1,2-dichloro-ethane at 20℃; for 0.583333h;
71%	With montmorillonite K-10 In benzene at 20℃; for 4h;	Typical Procedure for the Synthesis of 3a General procedure: To a stirred solution of 1 and 2 in benzene (1.5 mL) was added montmorillonite K-10 (500 mg), and the reaction mixture was stirred at room temperature for 4 h. After filtering off the solid materials and column chromatographic purification process (hexanes/THF, 20:1) compound 3 was obtained.
59%	With toluene-4-sulfonic acid In acetonitrile at 20℃; regioselective reaction;

Reference： [1]Yadav; Subba Reddy; Raghavendra Rao; Narayana Kumar [Synthesis, 2007, # 20, p. 3205 - 3210]
[2]Lim, Jin Woo; Kim, Se Hee; Kim, Jimin; Kim, Jae Nyoung [Bulletin of the Korean Chemical Society, 2015, vol. 36, # 5, p. 1351 - 1359]
[3]Location in patent: experimental part Sanz, Roberto; Gohain, Mukut; Miguel, Delia; Martínez, Alberto; Rodríguez, Félix [Synlett, 2009, # 12, p. 1985 - 1989]

16
[ 2362-62-1 ]
[ 1817-49-8 ]
[ 1239496-94-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With silver trifluoromethanesulfonate In chlorobenzene Reflux;

Reference： [1]Gao, Xun; Pan, Ying-Ming; Lin, Min; Chen, Li; Zhan, Zhuang-Ping [Organic and Biomolecular Chemistry, 2010, vol. 8, # 14, p. 3259 - 3266]

17
[ 58458-85-8 ]
[ 100-52-7 ]
[ 1817-49-8 ]

Yield	Reaction Conditions	Operation in experiment
	With C₂₀H₁₂O₂^(2-)*2K⁽¹⁺⁾ In tetrahydrofuran; hexane at 0℃;

Reference： [1]Location in patent: body text Ueda, Tomohiro; Tanaka, Kana; Ichibakase, Tomonori; Orito, Yuya; Nakajima, Makoto [Tetrahedron, 2010, vol. 66, # 39, p. 7726 - 7731]

18
[ 622-46-8 ]
[ 1817-49-8 ]
[ 1280577-47-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2011,vol. 353,p. 469 - 474

19
[ 1817-49-8 ]
[ 156136-55-9 ]
[ 1310025-09-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With toluene-4-sulfonic acid In nitromethane at 90℃; for 5h;

Reference： [1]Location in patent: experimental part Reddy, Chada Raji; Jithender, Enukonda; Krishna, Gaddam; Reddy, Gunreddy Venkat; Jagadeesh, Bharatam [Organic and Biomolecular Chemistry, 2011, vol. 9, # 10, p. 3940 - 3947]

20
[ 1817-49-8 ]
[ 54370-00-2 ]
[ 1354640-62-2 ]

Reference： [1]Synlett,2011,p. 2733 - 2739

21
[ 10201-71-5 ]
[ 1817-49-8 ]
[ 1356074-51-5 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 7308 - 7316

22
[ 1817-49-8 ]
[ 21717-95-3 ]
[ 1245815-62-6 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 7308 - 7316

23
[ 1817-49-8 ]
[ 149739-65-1 ]
[ 1373254-11-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 3538 - 3555

24
[ 1817-49-8 ]
[ 113-00-8 ]
[ 40230-24-8 ]

Reference： [1]Heterocycles,2012,vol. 85,p. 1891 - 1896

25
[ 1817-49-8 ]
[ 17422-32-1 ]
[ 1393095-21-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With aluminium(III) triflate In acetonitrile at 85℃; for 2h;	General reaction procedure: General procedure: Al(OTf)3 (2 mol %) was added to a solution of the indole 1 (1 mmol) and alkynol 2 (1.15 mmol, 1.15 equiv) in CH3CN (2.00 ml) and the reaction mixture was refluxed with stirring for the time indicated in Table 2. After completion of the reaction (monitored by GC-MS), the solvent was removed in vacuo and the residue purified by column chromatography on silica gel (EtOAc:hexane 5:95, v/v). All obtained products were fully characterized by spectroscopic analysis (1H NMR, 13C NMR and MS). The physical data of known compounds were identical to those published (see references in Table 2).

Reference： [1]Location in patent: experimental part Gohain, Mukut; Marais, Charlene; Bezuidenhoudt, Barend C.B. [Tetrahedron Letters, 2012, vol. 53, # 35, p. 4704 - 4707]

26
[ 1817-49-8 ]
[ 1593-60-8 ]
[ 1415035-26-5 ]

Yield	Reaction Conditions	Operation in experiment
38%	With iodine; In dichloromethane; water; at 25℃; for 3h;	General procedure: To a solution of propargyl alcohol 1 (0.6 mmol) and N-tosyl hydroxylamine 2 (0.5 mmol) in wet DCM (5 mL) was added I2 (1.0 mmol) slowly at 25 C, and the reaction mixture was stirred at a shown temperature for an indicated period of time shown in text. Saturated aqueous Na2S2O3 was added to quench the reaction and the mixture was extracted with DCM. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The residue was purified flash column chromatography on silica gel with DCM/hexane as eluent to give 4 or 5.400.0971.

Reference： [1]European Journal of Organic Chemistry,2012,p. 5767 - 5773
[2]Tetrahedron,2012,vol. 68,p. 10194 - 10200,7

27
[ 29906-67-0 ]
[ 1817-49-8 ]
[ 1373883-88-5 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 9510 - 9520

28
[ 1817-49-8 ]
[ 1145-01-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With N-iodo-succinimide; trifluorormethanesulfonic acid; hydrazine hydrate; In toluene; at 111℃; for 5h;Sealed tube;	The preparation process is as follows: adding a propargyl alcohol derivative, a halogen source and an acid in a sealed tube, and carrying out the reaction under the condition of heating under reflux at 111 C; and adding hydrazine after monitoring that the propargyl alcohol derivative has completely disappeared by TLC,After 5 hours of reaction, saturated brine was added to quench the reaction. The organic phase was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated to obtain a pyrazole derivative. The purity of the product was improved by column chromatography. Among them, propargyl alcohol, halogen source, hydrazine, solvent and acid were added as 1,3-diphenylprop-2-yn-1-ol (2 mmol), NIS (2 mmol), hydrazine hydrate (2.8 mmol), Toluene (10 mL) and trifluoromethanesulfonic acid (0.3 mmol).

Reference： [1]Patent: CN110483400,2019,A .Location in patent: Paragraph 0111-0115
[2]Chemistry - A European Journal,2012,vol. 18,p. 15602 - 15606
[3]Synthesis,2013,vol. 45,p. 830 - 836

29
[ 1484-12-4 ]
[ 1817-49-8 ]
[ 1421675-00-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With trifluorormethanesulfonic acid at 0 - 20℃; for 4h; Ionic liquid; Inert atmosphere; Schlenk technique;	3,6-bis(1,3-diphenylprop-2-ynyl)-9-methyl-9H-carbazole (4) General procedure: An oven-dried Schlenk tube was charged with (bmim)PF6 (4.0 mL) and N-methylimidazole (1 mmol). Propargyl alcohol (2.2 mmol) was added followed by triflic acid (0.1 mmol) under N2 atmosphere at 0 oC and the mixture was magnetically stirred at r.t. until completion (monitored by TLC). Once the reaction was over, the contents were cooled to r. t. and extracted with with EtOAc-Hexane (2:3 vol/vol) until the final extraction did not show a spot corresponding to the starting material or to the product. The combined organic extracts were washed with DI water, dried with MgSO4 and concentrated to give the crude product, which upon purification through column chromatography furnished the desired products. 3,6-bis(1,3-diphenylprop-2-ynyl)-9-methyl-9H-carbazole (4): Light yellow solid, m.p. 214-216 °C, Yield: 89%. 1H NMR (500 MHz, CDCl3): δH 3.80 (s, 3H), 5.41 (s, 2H), 7.20-7.33 (m, 15H), 7.48-7.52 (m, 9H), 8.14 (d, J = 1.5 Hz, 2H); 13C NMR (125 MHz, CDCl3): δC 29.35, 43.87, 85.00, 91.15, 108.83, 119.84, 122.92, 123.85, 126.13, 126.84, 128.01, 128.06, 128.35, 128.68, 131.85, 132.59, 140.59, 142.71 ppm; IR (cm-1, CHCl3): ν 3080, 3059, 3026, 1597, 1475, 1467, 1452, 1442, 1336, 1317, 1251, 1155, 1126, 1028, 914, 881, 798, 754; APCI-MS: 562 [M+H]+

Reference： [1]Kumar, G.G.K.S. Narayana; Laali, Kenneth K. [Tetrahedron Letters, 2013, vol. 54, # 8, p. 965 - 969]

30
[ 1817-49-8 ]
[ 619-55-6 ]
[ 1442693-06-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With Amberlite IR-120H In acetonitrile at 60℃; for 3h; regioselective reaction;	General experimental procedure General procedure: to a stirred mixture of arylpropargy alcohol 1 (1 mmol) and nucleophile (1.2 mmol) was added Amberlite IR-120H resin (0.3 g) in acetonitrile (5 mL). The mixture was stirred at rt -60 °C (Table 1) for an appropriate time. When the reaction was complete (GC and TLC analyses), the mixture was filtered and evaporated to dryness in vacuo to yield the crude product, which was purified by silicagel column chromatography (EtOAc-hexane).
78%	With gold(III) tribromide; silver trifluoromethanesulfonate In toluene for 1h; Reflux;	Procedure for the synthesis of 2,4-diphenyl-5-[(trimethylsilyl)methyl]oxazole (4aa): General procedure: AuBr3 (5.4 mg,0.012 mmol, 5 mol%) and AgOTf (9.4 mg, 0.037 mmol, 15 mol%) were added to a solution of3-trimethylsilylpropargylic alcohols 1 (50 mg, 0.25 mmol) and benzamide (2a) (36 mg, 0.29 mmol)in toluene (3 mL) at room temperature and the mixture was heated at reflux. After completeconsumption of propargylic substitution product 3aa (the reaction was monitored by thin layerchromatography), the solvent was removed in vacuo and the crude product was subjected to columnchromatography on silica gel (hexane:AcOEt = 30:1) to give 2,4-diphenyl-5-[(trimethylsilyl)methyl]oxazole (4aa) (53 mg, 75%) as colorless oil.

Reference： [1]Gujarathi, Satheesh; Hendrickson, Howard P.; Zheng, Guangrong [Tetrahedron Letters, 2013, vol. 54, # 27, p. 3550 - 3553]
[2]Morita, Nobuyoshi; Sano, Aoi; Sone, Ayako; Aonuma, Shino; Matsunaga, Arisa; Hashimoto, Yoshimitsu; Tamura, Osamu [Heterocycles, 2018, vol. 97, # 2, p. 719 - 728]

31
[ 623-17-6 ]
[ 1817-49-8 ]
[ 1610501-62-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With p-nitrobenzenesulfonic acid; In acetonitrile; at 20℃; for 0.5h;Inert atmosphere;	General procedure: A solution of substituted propargyl alcohol (1 mmol) and nucleophile (1.20 mmol) in acetonitrile (5 mL) was taken in round bottom flask (RBF) under nitrogen atmosphere and then p-NBSA (5 mol %) added at room temperature (rt). The reaction mixture was stirred at the same temperature and the progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was quenched by 10% of aq. NaHCO3 solution, extracted with ethyl acetate, further the combined ethyl acetate layer was washed using brine solution. The ethyl acetate layer was dried over Na2SO4, filtered and then filtrate was treated with silica gel (2g) for 30 minutes. Finally, the silica gel was filtered and the filtrate was concentrated under vacuum to obtain the desired product.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 3213 - 3217

32
[ 5335-87-5 ]
[ 1817-49-8 ]
2-[(4-methoxyphenyl)thio]-3-phenyl-1H-inden-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With dipotassium peroxodisulfate; iodine; acetic acid; dibenzoyl peroxide at 120℃; for 24h; Inert atmosphere; Schlenk technique;
76%	With dipotassium peroxodisulfate; iodine; dibenzoyl peroxide In acetic acid at 120℃; for 24h; Inert atmosphere;	3 Specific Example 3: 41.6 mg (0.2 mmol) of 1,3-diphenylpropynol, 55.7 mg (0.2 mmol) bis(4-methoxyphenyl)disulfide, 14.5 mg (0.06 mmol) of benzoyl peroxide, 101.6 mg (0.4 mmol) of iodine, 108.1 mg (0.4 mmol) of potassium persulfate was added to the reaction tube, 2 mL of acetic acid was added, and the reaction tube was filled with N2. 120 ° C for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, the organic layer was dried over anhydrous MgSO4, filtered and the filtrate was evaporated to dryness. The solvent was removed and the residue was chromatographed on silica gel using a petroleum ether and ethyl acetate volume ratio of 200: 1 mixture of the eluent, the effluent was collected according to the actual gradient, TLC detected, and the product-containing effluent was combined. The solvent was distilled off on a rotary evaporator and dried in vacuo to give a red solid 52.3 mg of 2-(4-methoxyphenylthio)-3-phenylinden-1-one in 76% yield.

Reference： [1]Zhang, Xing-Song; Jiao, Jun-Ying; Zhang, Xiao-Hong; Hu, Bo-Lun; Zhang, Xing-Guo [Journal of Organic Chemistry, 2016, vol. 81, # 13, p. 5710 - 5716]
[2]Current Patent Assignee: WENZHOU UNIVERSITY - CN105622470, 2016, A Location in patent: Paragraph 0029

33
[ 1817-49-8 ]
[ 14135-38-7 ]
2-[(2-fluorophenyl)thio]-3-phenyl-1H-inden-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With dipotassium peroxodisulfate; iodine; dibenzoyl peroxide; In nitromethane; at 120℃; for 24h;Inert atmosphere;	41.6 mg (0.2 mmol) of 1,3-diphenylpropynol, 50.9 mg (0.2 mmol) of bis(2-fluorophenyl)disulfide 14.5 mg (0.06 mmol) of benzoyl peroxide, 101.6 mg (0.4 mmol) of iodine, 108.1 mg (0.4 mmol) of potassium persulfate was added to the reaction tube, 2 mL of nitromethane was added, and the reaction tube was filled with N2. 120 ° C for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, the organic layer was dried over anhydrous MgSO4, filtered and the filtrate was evaporated to dryness. The solvent was removed and the residue was chromatographed on silica gel using a petroleum ether and ethyl acetate volume ratio of 200: 1 mixture of the eluent, the effluent was collected according to the actual gradient, TLC detected, and the product-containing effluent was combined. The solvent was distilled off on a rotary evaporator and dried in vacuo to give 40.6 mg of 2-(2-fluorophenylthio)-3-phenylinden-1-one as a red solid in 61percent yield.

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 5710 - 5716
[2]Patent: CN105622470,2016,A .Location in patent: Paragraph 0030

34
[ 1817-49-8 ]
[ 137897-99-5 ]
2-[(3,5-dichlorophenyl)thio]-3-phenyl-1H-inden-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With dipotassium peroxodisulfate; iodine; dibenzoyl peroxide In nitromethane at 120℃; for 24h; Inert atmosphere; Schlenk technique;
55%	With dipotassium peroxodisulfate; iodine; dibenzoyl peroxide In nitromethane at 120℃; for 24h; Inert atmosphere;	8 Specific Example 8: 41.6 mg (0.2 mmol) of 1,3-diphenylpropynol, 71.2 mg (0.2 mmol) of bis(3,5-dichlorophenyl)disulfide, 14.5 mg (0.06 mmol) of benzoyl peroxide, 101.6 mg (0.4 mmol) of iodine, 108.1 mg (0.4 mmol) of potassium persulfate was added to the reaction tube, 2 mL of nitromethane was added, and the reaction tube was filled with N2. 120 ° C for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, the organic layer was dried over anhydrous MgSO4, filtered and the filtrate was evaporated to dryness. The solvent was removed and the residue was chromatographed on silica gel using a petroleum ether and ethyl acetate volume ratio of 200: 1 mixture of the eluent, the effluent was collected according to the actual gradient, TLC detected, and the product-containing effluent was combined. The solvent was distilled off on a rotary evaporator and dried in vacuo to give 42.2 mg of a red oily liquid 2-(3,5-dichlorophenylthio)-3-phenylinden-1-one in a yield of 55%.

Reference： [1]Zhang, Xing-Song; Jiao, Jun-Ying; Zhang, Xiao-Hong; Hu, Bo-Lun; Zhang, Xing-Guo [Journal of Organic Chemistry, 2016, vol. 81, # 13, p. 5710 - 5716]
[2]Current Patent Assignee: WENZHOU UNIVERSITY - CN105622470, 2016, A Location in patent: Paragraph 0034

35
[ 100-32-3 ]
[ 1817-49-8 ]
2-[(4-nitrophenyl)thio]-3-phenyl-1H-inden-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With dipotassium peroxodisulfate; iodine; dibenzoyl peroxide; In nitromethane; at 120℃; for 24h;Inert atmosphere;	41.6 mg (0.2 mmol) of 1,3-diphenylpropynol, 61.7 mg (0.2 mmol) of bis(4-nitrophenyl)disulfide, 14.5 mg (0.06 mmol) of benzoyl peroxide, 101.6 mg (0.4 mmol) of iodine, 108.1 mg (0.4 mmol) of potassium persulfate was added to the reaction tube, 2 mL of nitromethane was added, and the reaction tube was filled with N2. 120 C for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, the organic layer was dried over anhydrous MgSO4, filtered and the filtrate was evaporated to dryness. The solvent was removed and the residue was chromatographed on silica gel using a petroleum ether and ethyl acetate volume ratio of 200: 1 mixture of the eluent, the effluent was collected according to the actual gradient, TLC detected, and the product-containing effluent was combined. The solvent was distilled off on a rotary evaporator and dried in vacuo to give a yellow solid 48.2 mg of 2-(4-nitrophenylthio)-3-phenylinden-1-one in 67% yield.

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 5710 - 5716
[2]Patent: CN105622470,2016,A .Location in patent: Paragraph 0035

36
[ 562-46-9 ]
[ 1817-49-8 ]
(Z)-3-benzylidene-7,7-dimethyl-2-phenyl-3,5,6,7-tetrahydrobenzofuran-4(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With boric acid; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 100℃; for 2h;Inert atmosphere;	General procedure: Synthesis of 3aa (Table 3, entry 4). A stirred solution of Pd(OAc)2 (5.8mg, 26mumol) and BINAP (32mg, 51mumol) in dioxane (1.0mL) was heated to 100C, and stirring was continued for 5min. After the resulting solution was cooled to rt, propargylic alcohol 1a (54mg, 257mumol), 1,3-cyclohexanedione (2a) (35mg, 308mumol) and boric acid (3.2mg, 51mumol) in dioxane (1.6mL) were added. The reaction mixture was then allowed to heat to 100C, and stirring was continued for 2h. After filtration of the reaction mixture using small amount of silica gel followed by concentration, the residue was chromatographed on silica gel with hexane-AcOEt (80:20 v/v) as eluent to give 3aa (66mg, 84% yield).

Reference： [1]Tetrahedron,2016,vol. 72,p. 5633 - 5639

37
[ 1817-49-8 ]
[ 50405-45-3 ]
(Z)-3-benzylidene-6,7-dimethyl-2-phenyl-2,3-dihydro-4H-furo[3,2-c]pyran-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With boric acid; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 100℃; for 2h;Inert atmosphere;	General procedure: Synthesis of 3aa (Table 3, entry 4). A stirred solution of Pd(OAc)2 (5.8mg, 26mumol) and BINAP (32mg, 51mumol) in dioxane (1.0mL) was heated to 100C, and stirring was continued for 5min. After the resulting solution was cooled to rt, propargylic alcohol 1a (54mg, 257mumol), 1,3-cyclohexanedione (2a) (35mg, 308mumol) and boric acid (3.2mg, 51mumol) in dioxane (1.6mL) were added. The reaction mixture was then allowed to heat to 100C, and stirring was continued for 2h. After filtration of the reaction mixture using small amount of silica gel followed by concentration, the residue was chromatographed on silica gel with hexane-AcOEt (80:20 v/v) as eluent to give 3aa (66mg, 84% yield).

Reference： [1]Tetrahedron,2016,vol. 72,p. 5633 - 5639

38
[ 700-12-9 ]
[ 1817-49-8 ]
3-(2,3,4,5,6-pentamethylphenyl)-1-phenyl-1H-indene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With gold(III) bromide In 2,2,2-trifluoroethanol for 1.5h; Reflux;	Gold-catalyzed synthesis of 1,3-diarylindenes 3 from propargylic alcohols 1 and aromatic compounds 2 General procedure: AuBr3 (5 mol%) was added to a stirred solution of propargylic alcohols 1 and aromatic compounds 2 in CF3CH2OH at room temperature, and the mixture was stirred at reflux for 1.5 h (the reaction was monitored by thin-layer chromatography, TLC). After addition of water and extraction with diethyl ethers (three times), the combined organic layers were washed once with brine and dried with Na2SO4. The solvent was removed in vacuo. The residue was purified by flash column chromatography on silica gel with hexane as eluent to afford indenes 3.
56%	With gold(III) bromide In 2,2,2-trifluoroethanol at 80℃; for 1.5h; Inert atmosphere;

Reference： [1]Morita, Nobuyoshi; Miyamoto, Masazumi; Yoda, Akiyoshi; Yamamoto, Mari; Ban, Shintaro; Hashimoto, Yoshimitsu; Tamura, Osamu [Tetrahedron Letters, 2016, vol. 57, # 40, p. 4460 - 4463]
[2]Jónsson, Helgi Freyr; Solvi, Thomas Nordbø; Lomeland, Sondre; Reiersølmoen, Ann Christin; Fiksdahl, Anne [ChemistryOpen, 2022, vol. 11, # 5]

39
[ 717-74-8 ]
[ 1817-49-8 ]
1-phenyl-3-(2,4,6-triisopropylphenyl)-1H-indene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With gold(III) bromide; In 2,2,2-trifluoroethanol; for 1.5h;Reflux;	General procedure: AuBr3 (5 mol%) was added to a stirred solution of propargylic alcohols 1 and aromatic compounds 2 in CF3CH2OH at room temperature, and the mixture was stirred at reflux for 1.5 h (the reaction was monitored by thin-layer chromatography, TLC). After addition of water and extraction with diethyl ethers (three times), the combined organic layers were washed once with brine and dried with Na2SO4. The solvent was removed in vacuo. The residue was purified by flash column chromatography on silica gel with hexane as eluent to afford indenes 3.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 4460 - 4463
[2]ChemistryOpen,2022

40
[ 1817-49-8 ]
[ 10531-80-3 ]
C₂₃H₁₉NO₂ [ No CAS ]