Synthesis of CF3-Containing Isoindolinone Derivatives through Rhodium-catalyzed Oxidative Coupling of Benzamides with 2-Trifluoromethylacrylate

被引：4

作者：

Yoshimoto, Risa ^{[1
]}

Morisaka, Hideaki ^{[1
]}

Usuki, Yoshinosuke ^{[1
]}

Shibata, Yu ^{[2
]}

Tanaka, Ken ^{[2
]}

Satoh, Tetsuya ^{[1
]}

机构：

[1] Osaka City Univ, Grad Sch Sci, Dept Chem, Sumiyoshi Ku, 3-3-138 Sugimoto, Osaka 5588585, Japan

[2] Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Meguro Ku, Tokyo 1528550, Japan

来源：

CHEMISTRY LETTERS | 2020年 / 49卷 / 12期

关键词：

Rhodium catalyst; Oxidative coupling; Isoindolinone; H BOND ACTIVATION; ALKYNES; ALKENES; AMINOTRIFLUOROMETHYLATION; FUNCTIONALIZATION; CONSTRUCTION;

D O I：

10.1246/cl.200609

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The oxidative coupling of benzamides with methyl 2-trifluoromethylacrylate proceeds smoothly under rhodium(III) catalysis to produce trifluoromethyl-substituted isoindolinone derivatives. The catalyst system [(CpRhCl2)-Rh-E](2)/AgSbF6 is effective for the oxidative coupling, while [Cp*RhCl2](2)/AgSbF6 leads to their redox-neutral coupling predominantly. The oxidative coupling reactions with related acrylates have also been examined.

引用

收藏

页码：1481 / 1483

页数：3

相关论文

共 50 条

[41] A Concise Total Synthesis of Pyrovellerolactone Using a Rhodium-Catalyzed [(3+2)+2] Carbocyclization Reaction [J].

Evans, P. Andrew ;

Inglesby, Phillip A. ;

Kilbride, Kathryn .

ORGANIC LETTERS, 2013, 15 (08) :1798-1801

[42] Rhodium-catalyzed synthesis of 2,3-diaryl-1,4-diketones via oxidative coupling of benzyl ketones using α-thioketone oxidizing reagent [J].

Arisawa, Mieko ;

Li, Guangzhe ;

Yamaguchi, Masahiko .

TETRAHEDRON LETTERS, 2013, 54 (10) :1298-1301

[43] Concise Total Synthesis of (-)-Vermiculine through a Rhodium-Catalyzed C2-Symmetric Dimerization Strategy [J].

Steib, Philip ;

Breit, Bernhard .

CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (14) :3532-3535

[44] Metal-free, Visible-Light-Induced Radical Trifluoromethylation/Cyclization of N-benzamides with CF3SO2Na to Synthesize CF3-Containing Isoquinoline-1,3-diones [J].

Wang, Shaowei ;

Dai, Peng ;

Yan, Zhichao ;

Wang, Youjia ;

Shao, Jiaxuan ;

Wu, Yanhui ;

Deng, Chao ;

Zhang, Weihua .

CHEMISTRYSELECT, 2019, 4 (35) :10329-10333

[45] Flexible Synthesis of Fused Benzofuran Derivatives by Rhodium-Catalyzed [2+2+2] Cycloaddition with Phenol-Linked 1,6-Diynes [J].

Komine, Yoshiyuki ;

Kamisawa, Akiyoshi ;

Tanaka, Ken .

ORGANIC LETTERS, 2009, 11 (11) :2361-2364

[46] Synthesis of β-CF3 Ketones through Copper/Silver Cocatalyzed Oxidative Coupling of Enol Acetates with ICH2CF3 [J].

Xiong, Yi ;

Chen, De ;

Zeng, Sheng ;

Cheng, Chaozhihui ;

Wang, Pengjie ;

Deng, Wei ;

Xiang, Jiannan ;

Yi, Niannian .

SYNLETT, 2018, 29 (17) :2279-2282

[47] Enantioselective Synthesis of CF3-Containing 3,2′-Pyrrolidinyl Spirooxindoles and Dispirooxindoles via Thiourea-Catalyzed Domino Michael/Mannich [3+2] Cycloaddition Reactions [J].

Lin, Ye ;

Song, Yong-Xing ;

Du, Da-Ming .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (05) :1064-1070

[48] A Synthesis of 3,4-Dihydroisoquinolin-1(2H)-one via the Rhodium-Catalyzed Alkylation of Aromatic Amides with N-Vinylphthalimide [J].

He, Qiyuan ;

Chatani, Naoto .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21) :13587-13594

[49] Rhodium-Catalyzed Merging of 2-Arylquinazolinone and 2,2-Difluorovinyl Tosylate: Diverse Synthesis of Monofluoroolefin Quinazolinone Derivatives [J].

Wang, Ning ;

Yang, Qin ;

Deng, Zhihong ;

Mao, Xuechun ;

Peng, Yiyuan .

ACS OMEGA, 2020, 5 (24) :14635-14644

[50] Copper-catalyzed radical cascade cyclization for synthesis of CF3-containing tetracyclic benzimidazo[2,1-a]iso-quinolin-6(5H)-ones [J].

Sun, Kai ;

Li, Guofeng ;

Guo, Sa ;

Zhang, Zhiguo ;

Zhang, Guisheng .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (02) :375-378

← 1 2 3 4 5 →