Alkene Trifluoromethylation Coupled with CC Bond Formation: Construction of Trifluoromethylated Carbocycles and Heterocycles

被引：253

作者：

Egami, Hiromichi ^{[1
,2
]}

Shimizu, Ryo ^{[1
,3
]}

Kawamura, Shintaro ^{[1
,2
]}

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

机构：

[1] RIKEN, Synthet Organ Chem Lab, 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：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 14期

关键词：

alkene; copper; fluorine; heterocycles; homogeneous catalysis; COPPER-CATALYZED TRIFLUOROMETHYLATION; ENANTIOSELECTIVE ALPHA-TRIFLUOROMETHYLATION; PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; ELECTROPHILIC TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; ROOM-TEMPERATURE; RADICAL TRIFLUOROMETHYLATION; PHOTOREDOX CATALYSIS; MEDICINAL CHEMISTRY; TERMINAL ALKENES;

D O I：

10.1002/anie.201210250

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The combo pack: Copper-catalyzed trifluoromethylation of alkenes bearing an allylic proton combined with C-C bond formation affords the title compounds in good to high yields (see scheme). The reactions are faster than allylic trifluoromethylation, especially in 1,4-dioxane. A unique 1,6- oxytrifluoromethylation occurred instead of an anticipated seven-membered ring forming carbotrifluoromethylation reaction. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4000 / 4003

页数：4

共 86 条

[1] The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes
Allen, Anna E.
MacMillan, David W. C.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) : 4986 - +
[2] Recent Progress in Catalytic Aromatic Trifluoromethylation
Amii, Hideki
[J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2011, 69 (07) : 752 - 762
[3] [Anonymous], 2005, ANGEW CHEM
[4] [Anonymous], 2009, Angew. Chem., Int. Ed.
[5] [Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1135/CCCC2011078
[6] A xanthate transfer radical process for the introduction of the trifluoromethyl group
Bertrand, F
Pevere, V
Quiclet-Sire, B
Zard, SZ
[J]. ORGANIC LETTERS, 2001, 3 (07) : 1069 - 1071
[7] Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine
[8] The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles
Chemler, Sherry R.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (15) : 3009 - 3019
[9] The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides
Cho, Eun Jin
Senecal, Todd D.
Kinzel, Tom
Zhang, Yong
Watson, Donald A.
Buchwald, Stephen L.
[J]. SCIENCE, 2010, 328 (5986) : 1679 - 1681
[10] Copper-Catalyzed Oxidative Trifluoromethylation of Terminal Alkenes Using Nucleophilic CF3SiMe3: Efficient C(sp3)-CF3 Bond Formation
Chu, Lingling
Qing, Feng-Ling
[J]. ORGANIC LETTERS, 2012, 14 (08) : 2106 - 2109

← 1 2 3 4 5 6 7 8 9 →