Perhaloalkylation of Metal Enolates-Unconventional and Versatile

被引：19

作者：

Amatov, Tynchtyk ^{[1
]}

Jahn, Ullrich ^{[1
]}

机构：

[1] Acad Sci Czech Republic, Inst Organ Chem & Biochem, CR-16610 Prague 6, Czech Republic

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 20期

关键词：

electron transfer; enols; perhaloalkylation; radical reactions; valence tautomerism; CATALYZED TRIFLUOROMETHYLATION; ALPHA-TRIFLUOROMETHYLATION; PERFLUOROALKYLATION;

D O I：

10.1002/anie.201007672

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Radically unconventional: Natural products with di- and trichloromethyl groups and trifluoromethylated pharmaceuticals and agrochemicials are interesting compounds, often with intriguing properties. These types of compounds can be prepared by the direct perhaloalkylation of carbonyl compounds in which enolate reactivity and radical reactivity are merged (see scheme; Bn=benzyl). © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4542 / 4544

页数：3

共 24 条

[1] [Anonymous], ANGEW CHEM
[2] Valence Tautomerism in Titanium Enolates: Catalytic Radical Haloalkylation and Application in the Total Synthesis of Neodysidenin
Beaumont, Stephane
Ilardi, Elizabeth A.
Monroe, Lucas R.
Zakarian, Armen
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) : 1482 - +
[3] Chlorosulfolipids: Structure, synthesis, and biological relevance
Bedke, D. Karl
Vanderwal, Christopher D.
[J]. NATURAL PRODUCT REPORTS, 2011, 28 (01) : 15 - 25
[4] 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
[5] The persistent radical effect: A principle for selective radical reactions and living radical polymerizations
Fischer, H
[J]. CHEMICAL REVIEWS, 2001, 101 (12) : 3581 - 3610
[6] Gu Z., 2010, ANGEW CHEM, V122, P9896
[7] Concise Total Synthesis of Sintokamides A, B, and E by a Unified, Protecting-Group-Free Strategy
Gu, Zhenhua
Zakarian, Armen
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (50) : 9702 - 9705
[8] DIASTEREOSELECTIVE PERFLUOROALKYLATION OF CHIRAL IMIDE ENOLATES WITH PERFLUOROALKYL IODIDES MEDIATED BY TRIETHYLBORANE
ISEKI, K
TAKAHASHI, M
ASADA, D
NAGAI, T
KOBAYASHI, Y
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1995, 74 (02) : 269 - 271
[9] Transition-Metal-Catalyzed Trifluoromethylation of Aryl Halides
Lundgren, Rylan J.
Stradiotto, Mark
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (49) : 9322 - 9324
[10] Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions
Ma, JA
Cahard, D
[J]. CHEMICAL REVIEWS, 2004, 104 (12) : 6119 - 6146

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