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

被引:62
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
[1]   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-+
[2]   Site-Selective Approach to -Fluorination: Photocatalyzed Ring Opening of Cyclopropanols [J].
Bloom, Steven ;
Bume, Desta Doro ;
Pitts, Cody Ross ;
Lectka, Thomas .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (22) :8060-8063
[3]   Photocatalyzed Benzylic Fluorination: Shedding "Light" on the Involvement of Electron Transfer [J].
Bloom, Steven ;
McCann, Michael ;
Lectka, Thomas .
ORGANIC LETTERS, 2014, 16 (24) :6338-6341
[4]   A photocatalyzed aliphatic fluorination [J].
Bloom, Steven ;
Knippel, James Levi ;
Lectka, Thomas .
CHEMICAL SCIENCE, 2014, 5 (03) :1175-1178
[5]   Metal-Catalyzed Benzylic Fluorination as a Synthetic Equivalent to 1,4-Conjugate Addition of Fluoride [J].
Bloom, Steven ;
Sharber, Seth Andrew ;
Holl, Maxwell Gargiulo ;
Knippel, James Levi ;
Lectka, Thomas .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (21) :11082-11086
[6]   Iron(II)-Catalyzed Benzylic Fluorination [J].
Bloom, Steven ;
Pitts, Cody Ross ;
Woltornist, Ryan ;
Griswold, Andrew ;
Holl, Maxwell Gargiulo ;
Lectka, Thomas .
ORGANIC LETTERS, 2013, 15 (07) :1722-1724
[7]   Chemoselective fluorination of 2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-ones using DAST [J].
Bonacorso, Helio G. ;
Porte, Liliane M. F. ;
Navarini, Jussara ;
Paim, Gisele R. ;
Luz, Fabio M. ;
Oliveira, Lenon M. ;
Whietan, Carson W. ;
Martins, Marcos A. P. ;
Zanatta, Nilo .
TETRAHEDRON LETTERS, 2011, 52 (26) :3333-3335
[8]   Monofluorination of Organic Compounds: 10 Years of Innovation [J].
Champagne, Pier Alexandre ;
Desroches, Justine ;
Hamel, Jean-Denys ;
Vandamme, Mathilde ;
Paquin, Jean-Francois .
CHEMICAL REVIEWS, 2015, 115 (17) :9073-9174
[9]  
Furuya T., 2008, Angew. Chem, V120, P6082, DOI DOI 10.1002/ANGE.200802164
[10]   Carbon-fluorine reductive elimination from a high-valent palladium fluoride [J].
Furuya, Takeru ;
Ritter, Tobias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (31) :10060-+