Oxytrifluoromethylation of multiple bonds using copper catalyst under mild conditions

被引：162

作者：

Egami, Hiromichi ^{[1
,2
]}

Shimizu, Ryo ^{[1
,3
]}

Sodeoka, Mikiko ^{[1
,2
,3
]}

机构：

[1] RIKEN, Adv Sci Inst, Wako, Saitama 3510198, Japan

[2] Japan Sci & Technol Agcy, ERATO, Sodeoka Live Cell Chem Project, Wako, Saitama 3510198, Japan

[3] Saitama Univ, Grad Sch Sci & Engn, Sakura Ku, Saitama 3388570, Japan

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 41期

关键词：

Trifluoromethylation; Copper; Olefin; Alkyne; Togni reagent; ENANTIOSELECTIVE ALPHA-TRIFLUOROMETHYLATION; ELECTROPHILIC TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; TERMINAL ALKENES; CARBOXYLIC-ACIDS; FLUORINATION; ARYL; PERFLUOROALKYLATION; ALDEHYDES; REAGENT;

D O I：

10.1016/j.tetlet.2012.07.134

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxytrifluoromethylation reaction of styrene derivatives and alkynes with external and internal oxygen nucleophiles, catalyzed by copper (1) salts under mild conditions, was developed. Direct formation of a beta-trifluoromethylstyrene derivative from a styrene derivative was also achieved by the reaction in the presence of a Bronsted acid. Further transformation of the oxytrifluoromethylated products was conducted to demonstrate their utility. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5503 / 5506

页数：4

共 69 条

[31] Copper-catalyzed trifluoromethylation of terminal alkynes using Umemoto's reagent [J].

Luo, Dong-Fen ;

Xu, Jun ;

Fu, Yao ;

Guo, Qing-Xiang .

TETRAHEDRON LETTERS, 2012, 53 (22) :2769-2772

[32] Update 1 of: Asymmetric Fluorination, Trifluoromethylation, and Perfluoroalkylation Reactions [J].

Ma, Jun-An ;

Cahard, Dominique .

CHEMICAL REVIEWS, 2008, 108 (09) :PR1-PR43

[33] Cinchona Alkaloids/TMAF combination-catalyzed nucleophilic enantioselective trifluoromethylation of aryl ketones [J].

Mizuta, Satoshi ;

Shibata, Norio ;

Akiti, Surendar ;

Fujimoto, Hiroyuki ;

Nakamura, Shuichi ;

Toru, Takeshi .

ORGANIC LETTERS, 2007, 9 (18) :3707-3710

[34] Trifluoromethylation of Allylsilanes under Copper Catalysis [J].

Mizuta, Satoshi ;

Galicia-Lopez, Oscar ;

Engle, Keary M. ;

Verhoog, Stefan ;

Wheelhouse, Katherine ;

Rassias, Gerasimos ;

Gouverneur, Veronique .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (28) :8583-8587

[35] Palladium-Catalyzed Oxidative Aryltrifluoromethylation of Activated Alkenes at Room Temperature [J].

Mu, Xin ;

Wu, Tao ;

Wang, Hao-yang ;

Guo, Yin-long ;

Liu, Guosheng .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) :878-881

[36] Palladium-Catalyzed Oxidative Trifluoromethylation of Indoles at Room Temperature [J].

Mu, Xin ;

Chen, Shujun ;

Zhen, Xingliang ;

Liu, Guosheng .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (22) :6039-6042

[37] Fluorine in pharmaceuticals:: Looking beyond intuition [J].

Mueller, Klaus ;

Faeh, Christoph ;

Diederich, Francois .

SCIENCE, 2007, 317 (5846) :1881-1886

[38] Asymmetric trifluoromethylation of ketones with (trifluoromethyl)trimethylsilane catalyzed by chiral quaternary ammonium phenoxides [J].

Nagao, Hitoshi ;

Yamane, Yoshinobu ;

Mukaiyama, Teruaki .

CHEMISTRY LETTERS, 2007, 36 (05) :666-667

[39] Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis [J].

Nagib, David A. ;

MacMillan, David W. C. .

NATURE, 2011, 480 (7376) :224-228

[40] Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis [J].

Nagib, David A. ;

Scott, Mark E. ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) :10875-+

← 1 2 3 4 5 6 7 →