Difunctionalization of Alkenes via the Visible-Light-Induced Trifluoromethylarylation/1,4-Aryl Shift/Desulfonylation Cascade Reactions

被引：127

作者：

Zheng, Lewei ^{[1
]}

Yang, Chao ^{[1
]}

Xu, ZhaoZhong ^{[1
]}

Gao, Fei ^{[1
]}

Xia, Wujiong ^{[1
]}

机构：

[1] Harbin Inst Technol, Acad Fundamental & Interdisciplinary Sci, State Key Lab Urban Water Resource & Environm, Harbin 150080, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 11期

关键词：

DRIVEN PHOTOREDOX CATALYSIS; MEDIATED TRIFLUOROMETHYLATION; SYNTHETIC APPLICATIONS; ACTIVATED ALKENES; ORGANIC-SYNTHESIS; BOND FORMATION; PHOTOCATALYSIS; HYDROTRIFLUOROMETHYLATION; OXYTRIFLUOROMETHYLATION; FUNCTIONALIZATION;

D O I：

10.1021/acs.joc.5b00677

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel visible-light-induced trifluoromethylarylation/1,4-aryl shift/desulfonylation cascade reaction using CF3SO2Cl as CF3 source was described. The protocol provides an efficient approach for the synthesis of alpha-aryl-beta-trifluoromethyl amides and/or CF3-containing oxindoles as well as the isoquinolinediones under benign conditions.

引用

页码：5730 / 5736

页数：7

共 56 条

[1]

Anna U., 2015, CHEM-EUR J, V21, P1444

[2] Tamed Arene and Heteroarene Trifluoromethylation [J].

Besset, Tatiana ;

Schneider, Cedric ;

Cahard, Dominique .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5048-5050

[3] CC-1065 and the duocarmycins: Synthetic studies [J].

Boger, DL ;

Boyce, CW ;

Garbaccio, RM ;

Goldberg, JA .

CHEMICAL REVIEWS, 1997, 97 (03) :787-828

[4] Trifluoromethylation of Alkenes with Concomitant Introduction of Additional Functional Groups [J].

Egami, Hiromichi ;

Sodeoka, Mikiko .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (32) :8294-8308

[5] Alkene Trifluoromethylation Coupled with CC Bond Formation: Construction of Trifluoromethylated Carbocycles and Heterocycles [J].

Egami, Hiromichi ;

Shimizu, Ryo ;

Kawamura, Shintaro ;

Sodeoka, Mikiko .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) :4000-4003

[6] Visible light-mediated oxidative quenching reaction to electron-rich epoxides: highly regioselective synthesis of α-bromo (di)ketones and mechanism study [J].

Guo, Lin ;

Yang, Chao ;

Zheng, Lewei ;

Xia, Wujiong .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (35) :5787-5792

[7] Copper-Mediated Trifluoromethylation of α-Diazo Esters with TMSCF3: The Important Role of Water as a Promoter [J].

Hu, Mingyou ;

Ni, Chuanfa ;

Hu, Jinbo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (37) :15257-15260

[8] Trifluoromethylation of Alkenes by Visible Light Photoredox Catalysis [J].

Iqbal, Naeem ;

Choi, Sungkyu ;

Kim, Eunjin ;

Cho, Eun Jin .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (24) :11383-11387

[9] Direct C-H Functionalization of Enamides and Enecarbamates by Using Visible-Light Photoredox Catalysis [J].

Jiang, Heng ;

Huang, Chengmei ;

Guo, Jiajia ;

Zeng, Chuanqi ;

Zhang, Yan ;

Yu, Shouyun .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (47) :15158-15166

[10] REACTION OF TRIFLUOROMETHANESULFONYL CHLORIDE WITH ALKENES CATALYZED BY A RUTHENIUM(II) COMPLEX [J].

KAMIGATA, N ;

FUKUSHIMA, T ;

YOSHIDA, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (20) :1559-1560

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