Trifluoromethylation of Allylsilanes under Copper Catalysis

被引：111

作者：

Mizuta, Satoshi ^{[1
]}

Galicia-Lopez, Oscar ^{[1
]}

Engle, Keary M. ^{[1
]}

Verhoog, Stefan ^{[1
]}

Wheelhouse, Katherine ^{[2
]}

Rassias, Gerasimos ^{[2
]}

Gouverneur, Veronique ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

[2] GlaxoSmithKline R&D, Med Discovery & Dev, Stevenage SG1 2NY, Herts, England

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 28期

基金：

英国工程与自然科学研究理事会;

关键词：

allylsilanes; copper; homogeneous catalysis; radicals; trifluoromethylation; ENANTIOSELECTIVE ALPHA-TRIFLUOROMETHYLATION; MILD ELECTROPHILIC TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; ALLYLIC FLUORIDES; SALT SYSTEM; REAGENTS; RADICALS; SILICON; BETA; CARBON;

D O I：

10.1002/chem.201201707

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Branched allylic CF 3 products are accessible by copper-catalyzed trifluoromethylation of allylsilanes with the Togni reagent I. The silyl group is critical to control the outcome of this reaction because in its absence, a product of addition between the alkene and the Togni reagent is formed preferentially. The reaction is inhibited with 2,2,6,6-tetramethyl-1- piperidinyloxy (TEMPO) and is likely to operate via multiple reaction pathways. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8583 / 8587

页数：5

共 65 条

[31] The New Age of Electrophilic Perfluoroalkylation Reactions
Mace, Yohan
Magnier, Emmanuel
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (13) : 2479 - 2494
[32] Synthesis of α-CF3-Substituted Carbonyl Compounds with Relative and Absolute Stereocontrol Using Electrophilic CF3-Transfer Reagents
Matousek, Vaclav
Togni, Antonio
Bizet, Vincent
Cahard, Dominique
[J]. ORGANIC LETTERS, 2011, 13 (21) : 5762 - 5765
[33] Matsnev A., 2010, Angew. Chem. Int. Ed, V122, P582
[34] Efficient Access to Extended Yagupolskii-Umemoto-Type Reagents: Triflic Acid Catalyzed Intramolecular Cyclization of ortho-Ethynylaryltrifluoromethylsulfanes
Matsnev, Andrej
Noritake, Shun
Nomura, Yoshinori
Tokunaga, Etsuko
Nakamura, Shuichi
Shibata, Norio
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (03) : 572 - 576
[35] Rhenium-Catalyzed Trifluoromethylation of Arenes and Heteroarenes by Hypervalent Iodine Reagents
Mejia, Esteban
Togni, Antonio
[J]. ACS CATALYSIS, 2012, 2 (04): : 521 - 527
[36] Palladium-Catalyzed Oxidative Trifluoromethylation of Indoles at Room Temperature
Mu, Xin
Chen, Shujun
Zhen, Xingliang
Liu, Guosheng
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (22) : 6039 - 6042
[37] Fluorine in pharmaceuticals:: Looking beyond intuition
Mueller, Klaus
Faeh, Christoph
Diederich, Francois
[J]. SCIENCE, 2007, 317 (5846) : 1881 - 1886
[38] Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis
Nagib, David A.
MacMillan, David W. C.
[J]. NATURE, 2011, 480 (7376) : 224 - 228
[39] Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis
Nagib, David A.
Scott, Mark E.
MacMillan, David W. C.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) : 10875 - +
[40] THE SOLUTION-PHASE PHOTOCHEMISTRY OF 2-TRIFLUOROMETHYLNORBORNENE
NGUYEN, N
HARRIS, BE
CLARK, KB
LEIGH, WJ
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (11): : 1961 - 1966

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