Oxytrifluoromethylation of multiple bonds using copper catalyst under mild conditions

被引：164

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

[61] Electrophilic trifluoromethylation of arenes and N-heteroarenes using hypervalent iodine reagents [J].

Wiehn, Matthias S. ;

Vinogradova, Ekaterina V. ;

Togni, Antonio .

JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (09) :951-957

[62] Recent Developments on the Trifluoromethylation of (Hetero)Arenes [J].

Wu, Xiao-Feng ;

Neumann, Helfried ;

Beller, Matthias .

CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (08) :1744-1754

[63] Copper-Catalyzed Trifluoromethylation of Terminal Alkenes through Allylic C-H Bond Activation [J].

Xu, Jun ;

Fu, Yao ;

Luo, Dong-Fen ;

Jiang, Yuan-Ye ;

Xiao, Bin ;

Liu, Zhao-Jing ;

Gong, Tian-Jun ;

Liu, Lei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (39) :15300-15303

[64] Copper-catalyzed trifluoromethylation of aryl boronic acids using a CF3+ reagent [J].

Xu, Jun ;

Luo, Dong-Fen ;

Xiao, Bin ;

Liu, Zhao-Jing ;

Gong, Tian-Jun ;

Fu, Yao ;

Liu, Lei .

CHEMICAL COMMUNICATIONS, 2011, 47 (14) :4300-4302

[65] Radical-mediated hydroxytrifluoromethylation of α,β-unsaturated esters [J].

Yajima, T ;

Nagano, H ;

Saito, C .

TETRAHEDRON LETTERS, 2003, 44 (37) :7027-7029

[66] Merging Visible-Light Photocatalysis and Transition-Metal Catalysis in the Copper-Catalyzed Trifluoromethylation of Boronic Acids with CF3I [J].

Ye, Yingda ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (22) :9034-9037

[67] Generation of the CF3 radical from trifluoromethylsulfonium triflate and its trifluoromethylation of styrenes [J].

Zhang, Cheng-Pan ;

Wang, Zong-Ling ;

Chen, Qing-Yun ;

Zhang, Chun-Tao ;

Gu, Yu-Cheng ;

Xiao, Ji-Chang .

CHEMICAL COMMUNICATIONS, 2011, 47 (23) :6632-6634

[68] An Improved Copper-Mediated Oxidative Trifluoromethylation of Terminal Alkynes [J].

Zhang, Ke ;

Qiu, Xiao-Long ;

Huang, Yangen ;

Qing, Feng-Ling .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (01) :58-61

[69] Combination Catalysis in Enantioselective Trifluoromethylation [J].

Zheng, Yan ;

Ma, Jun-An .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (16) :2745-2750

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