Palladium(II)-Catalyzed Selective Monofluorination of Benzoic Acids Using a Practical Auxiliary: A Weak-Coordination Approach

被引：166

作者：

Chan, Kelvin S. L. ^{[1
]}

Wasa, Masayuki ^{[1
]}

Wang, Xisheng ^{[1
]}

Yu, Jin-Quan ^{[1
]}

机构：

[1] Scripps Res Inst TSRI, Dept Chem, La Jolla, CA 92037 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 39期

关键词：

auxiliaries; benzoic acids; C-H activation; fluorination; weak coordination; C-H BONDS; CATALYTIC ENANTIOSELECTIVE FLUORINATION; REDUCTIVE ELIMINATION; ARYLATION; HALOGENATION; IODINATION; CHEMISTRY;

D O I：

10.1002/anie.201102985

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Finally, a choice! A highly selective palladium(II)-catalyzed ortho-monofluorination reaction has been achieved for the first time through a weak coordination (see scheme; Ar=2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl) . Simple modification of this protocol allows for a choice between mono- and difluorination. The mono- and difluorinated benzoic acid derivatives are valuable in the pharmaceutical and agrochemical industries. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9081 / 9084

页数：4

共 59 条

[1] Nucleophilic routes to selectively fluorinated aromatics
Adams, DJ
Clark, JH
[J]. CHEMICAL SOCIETY REVIEWS, 1999, 28 (04) : 225 - 231
[2] Anbarasan P., 2010, ANGEW CHEM, V122, P2265
[3] A New and Practical Grignard-Coupling-Fluorination Sequence: Synthesis of 2-Aryl Fluoroarenes
Anbarasan, Pazhamalai
Neumann, Helfried
Beller, Matthias
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (08) : 1775 - 1778
[4] Efficient Synthesis of Aryl Fluorides
Anbarasan, Pazhamalai
Neumann, Helfried
Beller, Matthias
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (12) : 2219 - 2222
[5] [Anonymous], 2005, ANGEW CHEM
[6] [Anonymous], ANGEW CHEM
[7] Synthesis and Reactivity of a Mono-σ-Aryl Palladium(IV) Fluoride Complex
Ball, Nicholas D.
Sanford, Melanie S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) : 3796 - +
[8] Direct organocatalytic α-fluorination of aldehydes and ketones
Enders, D
Hüttl, MRM
[J]. SYNLETT, 2005, (06) : 991 - 993
[9] Bystanding F+ Oxidants Enable Selective Reductive Elimination from High-Valent Metal Centers in Catalysis
Engle, Keary M.
Mei, Tian-Sheng
Wang, Xisheng
Yu, Jin-Quan
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (07) : 1478 - 1491
[10] Furuya T., 2008, Angew. Chem, V120, P6082, DOI DOI 10.1002/ANGE.200802164

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