Fluorine-Enabled Cationic Gold Catalysis: Functionalized Hydration of Alkynes

被引:144
作者
Wang, Weibo [1 ]
Jasinski, Jacek [2 ]
Hammond, Gerald B. [1 ]
Xu, Bo [1 ]
机构
[1] Univ Louisville, Dept Chem, Louisville, KY 40292 USA
[2] Univ Louisville, Conn Ctr Renewable Energy Res, Louisville, KY 40292 USA
基金
美国国家科学基金会;
关键词
alkynes; fluorination; fluoroketones; gold; CROSS-COUPLING REACTIONS; ARYLBORONIC ACIDS; BOND FORMATION; ALKENES; KETONES; SPECTROSCOPY; CYCLIZATION; REACTIVITY; MECHANISM; XPS;
D O I
10.1002/anie.201003593
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Fluorine makes it possible: A cationic fluorine-gold species generated by fluorination of a low-valence gold complex mediates the "functionalized hydration" of alkynes. A triple bond is used to install a carbonyl group and two new bonds on the a-carbon atom, all occurring in one pot, under mild conditions and in very good. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:7247 / 7252
页数:6
相关论文
共 59 条
[1]  
[Anonymous], 2003, ANGEW CHEM
[2]  
[Anonymous], ANGEW CHEM
[3]   Alternative synthetic methods through new developments in catalysis by gold [J].
Arcadi, Antonio .
CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325
[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]   A CONVENIENT SYNTHESIS OF BETA-KETO PHENYL SULFIDES FROM ALKYNES [J].
BENATI, L ;
MONTEVECCHI, PC ;
SPAGNOLO, P .
TETRAHEDRON LETTERS, 1988, 29 (19) :2381-2384
[6]  
Benitez D, 2009, NAT CHEM, V1, P482, DOI [10.1038/NCHEM.331, 10.1038/nchem.331]
[7]  
Brenzovich W. E., 2010, ANGEW CHEM, V122, P5651
[8]   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
[9]   XPS study of supported gold catalysts:: the role of Au0 and Au+δ species as active sites [J].
Casaletto, MP ;
Longo, A ;
Martorana, A ;
Prestianni, A ;
Venezia, AM .
SURFACE AND INTERFACE ANALYSIS, 2006, 38 (04) :215-218
[10]   RETRACTED: Rhodium-catalyzed arylative and alkenylative cyclization of 1,5-enynes induced by geminal carbometalation of alkynes (Retracted Article) [J].
Chen, Yiyun ;
Lee, Chulbom .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (49) :15598-15599