Comprehensive kinetic screening of palladium catalysts for Heck reactions

被引:18
作者
Blackmond, Donna G. [1 ]
Schultz, Thomas
Mathew, Jinu S.
Loew, Caroline
Rosner, Thorsten
Pfaltz, Andreas
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
[2] Univ London Imperial Coll Sci Technol & Med, Dept Chem Engn & Chem Technol, London SW7 2AZ, England
[3] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland
[4] Merck Res Labs, Dept Proc Res, Catalysis Grp, Rahway, NJ 07065 USA
关键词
Heck reactions; Pd; kinetic screening; reaction calorimetry;
D O I
10.1055/s-2006-951514
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Comprehensive kinetic screening of Pd catalysts for Heck reactions via a consecutive pulse reaction methodology allows a more informed choice of catalyst for a particular transformation, taking into account not only initial reactivity but also long-term catalyst stability. Competitive reactions also offer mechanistic information. The resting state and rate-limiting step within the catalytic cycle are found to be the same for phospha- and azapallada-cycles and ligandless Pd(OAc)(2) but different for the zero valent complex Pd[P(t-BU)(3)](2).
引用
收藏
页码:3135 / 3139
页数:5
相关论文
共 23 条
[1]   Palladacyclic catalysts in C-C and C-heteroatom bond-forming reactions [J].
Bedford, RB .
CHEMICAL COMMUNICATIONS, 2003, (15) :1787-1796
[2]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[3]   Reaction progress kinetic analysis: A powerful methodology for mechanistic studies of complex catalytic reactions [J].
Blackmond, DG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (28) :4302-4320
[4]   Comprehensive kinetic screening of catalysts using reaction calorimetry [J].
Blackmond, DG ;
Rosner, T ;
Pfaltz, A .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1999, 3 (04) :275-280
[5]  
Böhm VPW, 2001, CHEM-EUR J, V7, P4191
[6]  
Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222
[7]   High-turnover palladium catalysts in cross-coupling and Heck chemistry: A critical overview [J].
Farina, V .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1553-1582
[8]   PALLADIUM-CATALYZED VINYLIC HYDROGEN SUBSTITUTION REACTIONS WITH ARYL, BENZYL, AND STYRYL HALIDES [J].
HECK, RF ;
NOLLEY, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (14) :2320-&
[9]  
HECK RF, 1982, ORG REACTIONS, V27, P345
[10]  
Herrmann W. A., 1995, ANGEW CHEM, V107, P1989