Enantioselective Palladium-Catalyzed Oxidative β,β-Fluoroarylation of α,β-Unsaturated Carbonyl Derivatives

被引:63
作者
Miro, Javier [1 ]
del Pozo, Carlos [1 ]
Toste, F. Dean [2 ]
Fustero, Santos [1 ,3 ]
机构
[1] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Spain
[2] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[3] Ctr Invest Principe Felipe, Lab Mol Organ, Valencia 46012, Spain
关键词
alkenes; fluorine; palladium; reaction mechanisms; synthetic methods; ALPHA-AMINO-ACIDS; C-H BONDS; BENZYLIC FLUORINATION; NUCLEOPHILIC FLUORINATION; SELECTIVE FLUORINATION; REDUCTIVE ELIMINATION; PHASE-TRANSFER; BORONIC ACIDS; FLUORIDE; ALKENES;
D O I
10.1002/anie.201603046
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The site-selective palladium-catalyzed three-component coupling of deactivated alkenes, arylboronic acids, and N-fluorobenzenesulfonimide is disclosed herein. The developed methodology establishes a general, modular, and step-economical approach to the stereoselective beta-fluorination of alpha,beta-unsaturated systems.
引用
收藏
页码:9045 / 9049
页数:5
相关论文
共 60 条
[41]   The highest oxidation states of the transition metal elements [J].
Riedel, Sebastian ;
Kaupp, Martin .
COORDINATION CHEMISTRY REVIEWS, 2009, 253 (5-6) :606-624
[42]  
Romanov-Michailidis F., 2013, ANGEW CHEM, V125, P9436
[43]   Enantioselective halogenative semi-pinacol rearrangement: a stereodivergent reaction on a racemic mixture [J].
Romanov-Michailidis, Fedor ;
Pupier, Marion ;
Guenee, Laure ;
Alexakis, Alexandre .
CHEMICAL COMMUNICATIONS, 2014, 50 (88) :13461-13464
[44]   Enantioselective Organocatalytic Fluorination-Induced Wagner-Meerwein Rearrangement [J].
Romanov-Michailidis, Fedor ;
Guenee, Laure ;
Alexakis, Alexandre .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) :9266-9270
[45]   Pd(0)-Catalyzed 1,1-Diarylation of Ethylene and Allylic Carbonates [J].
Saini, Vaneet ;
Liao, Longyan ;
Wang, Qiaofeng ;
Jana, Ranjan ;
Sigman, Matthew S. .
ORGANIC LETTERS, 2013, 15 (19) :5008-5011
[46]   Palladium-Catalyzed 1,1-Difunctionalization of Ethylene [J].
Saini, Vaneet ;
Sigman, Matthew S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (28) :11372-11375
[47]  
Shiro M., 2008, ANGEW CHEM, V120, P4225
[48]   Selective and effective fluorination of organic compounds in water using Selectfluor F-TEDA-BF4 [J].
Stavber, G ;
Zupan, M ;
Jereb, M ;
Stavber, S .
ORGANIC LETTERS, 2004, 6 (26) :4973-4976
[49]   Asymmetric Palladium-Catalyzed Directed Intermolecular Fluoroarylation of Styrenes [J].
Talbot, Eric P. A. ;
Fernandes, Talita de A. ;
McKenna, Jeffrey M. ;
Toste, F. Dean .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (11) :4101-4104
[50]   Fluorine in Pharmaceutical Industry: Fluorine-Containing Drugs Introduced to the Market in the Last Decade (2001-2011) [J].
Wang, Jiang ;
Sanchez-Rosello, Maria ;
Luis Acena, Jose ;
del Pozo, Carlos ;
Sorochinsky, Alexander E. ;
Fustero, Santos ;
Soloshonok, Vadim A. ;
Liu, Hong .
CHEMICAL REVIEWS, 2014, 114 (04) :2432-2506