Asymmetric Palladium-Catalyzed Directed Intermolecular Fluoroarylation of Styrenes

被引：129

作者：

Talbot, Eric P. A. ^{[1
,2
]}

Fernandes, Talita de A. ^{[2
]}

McKenna, Jeffrey M. ^{[1
]}

Toste, F. Dean ^{[2
]}

机构：

[1] Novartis Inst Biomed Res, Horsham RH12 5AB, W Sussex, England

[2] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 11期

关键词：

ORGANOCATALYTIC ALPHA-FLUORINATION; ENANTIOSELECTIVE FLUORINATION; (Z)-4'-ACETOXY-2'-BUTENYL 2-ALKYNOATES; COUPLING REACTIONS; ACID DERIVATIVES; C-C; CARBON; OXYARYLATION; CYCLIZATION; ARYLATION;

D O I：

10.1021/ja412881j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A mild catalytic asymmetric direct fluoro-arylation of styrenes has been developed. The palladium-catalyzed three-component coupling of Selectfluor, a styrene and a boronic acid, provides chiral monofluorinated compounds in good yield and in high enantiomeric excess. A mechanism proceeding through a Pd(IV)-fluoride intermediate is proposed for the transformation and synthesis of an sp(3) C-F bond.

引用

页码：4101 / 4104

页数：4

共 79 条

[1] Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives [J].

Ano, Yusuke ;

Tobisu, Mamoru ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) :12984-12986

[2] Gold-Catalysed Oxyarylation of Styrenes and Mono- and gem-Disubstituted Olefins Facilitated by an Iodine(III) Oxidant [J].

Ball, Liam T. ;

Lloyd-Jones, Guy C. ;

Russell, Christopher A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (10) :2931-2937

[3] Arylsilanes: Application to Gold-Catalyzed Oxyarylation of Alkenes [J].

Ball, Liam T. ;

Green, Michael ;

Lloyd-Jones, Guy C. ;

Russell, Christopher A. .

ORGANIC LETTERS, 2010, 12 (21) :4724-4727

[4] Synthesis and Reactivity of a Mono-σ-Aryl Palladium(IV) Fluoride Complex [J].

Ball, Nicholas D. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) :3796-+

[5] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Sottocornola, Silvia .

CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365

[6] Enantioselective organocatalytic α-fluorination of aldehydes [J].

Beeson, TD ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) :8826-8828

[7] Fluorine in medicinal chemistry [J].

Böhm, HJ ;

Banner, D ;

Bendels, S ;

Kansy, M ;

Kuhn, B ;

Müller, K ;

Obst-Sander, U ;

Stahl, M .

CHEMBIOCHEM, 2004, 5 (05) :637-643

[8] Gold-Catalyzed Oxidative Coupling Reactions with Aryltrimethylsilanes [J].

Brenzovich, William E., Jr. ;

Brazeau, Jean-Francois ;

Toste, F. Dean .

ORGANIC LETTERS, 2010, 12 (21) :4728-4731

[9] Gold-Catalyzed Intramolecular Aminoarylation of Alkenes: C-C Bond Formation through Bimolecular Reductive Elimination [J].

Brenzovich, William E., Jr. ;

Benitez, Diego ;

Lackner, Aaron D. ;

Shunatona, Hunter P. ;

Tkatchouk, Ekaterina ;

Goddard, William A., III ;

Toste, F. Dean .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (32) :5519-5522

[10] Design, synthesis, and evaluation of a novel class of enantioselective electrophilic fluorinating agents:: N-fluoro ammonium salts of cinchona alkaloids (F-CA-BF4) [J].

Cahard, D ;

Audouard, C ;

Plaquevent, JC ;

Roques, N .

ORGANIC LETTERS, 2000, 2 (23) :3699-3701

← 1 2 3 4 5 6 7 8 →