Oxidative addition of Pd(0) to Ar-SO2R bonds:: Heck-type reactions of sulfones

被引:18
作者
Garcia Ruano, Jose Luis [1 ]
Aleman, Jose [1 ]
Garcia Paredes, Cristina [1 ]
机构
[1] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain
关键词
D O I
10.1021/ol060608y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phenyl vinyl sulfones and sulfoxides react with Pd(OAc)(2) to form styryl sulfoxides and sulfones according to the first Mizoroki-Heck reaction reported for these thio derivatives. Only sulfones are able to react by using catalytic amounts of Pd (up to 1 mol %) in the presence of Ag2CO3. 1,2-Diphenylsulfonyl ethenes, alkynylphenyl sulfones, and other sulfones, less prone to act as acceptors in the Heck-type reactions, can transfer the aryl group to alkyl acrylates forming cinnamic esters.
引用
收藏
页码:2683 / 2686
页数:4
相关论文
共 37 条
[1]   Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 1: The Heck reaction [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
TETRAHEDRON, 2005, 61 (50) :11771-11835
[2]   Comparative reactivity of palladium(0) complexes generated in situ in mixtures of triphenylphosphine or tri-2-furylphosphine and Pd(dba)2 [J].
Amatore, C ;
Jutand, A ;
Meyer, G ;
Atmani, H ;
Khalil, F ;
Chahdi, FO .
ORGANOMETALLICS, 1998, 17 (14) :2958-2964
[3]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[4]   RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].
CABRI, W ;
CANDIANI, I .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7
[5]   NICKEL-CATALYZED SUBSTITUTIONS OF ARYL TERT-BUTYL SULFONES WITH ORGANOMETALLIC REAGENTS - SYNTHESIS OF ORTHO-SUBSTITUTED UNSYMMETRICAL BIARYLS [J].
CLAYDEN, J ;
COONEY, JJA ;
JULIA, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (01) :7-14
[6]  
CRAMPTON MR, 1997, ORGANIC REACTION MEC, P1995
[7]  
CRIPS GT, 1998, CHEM SOC REV, V27, P427
[8]   FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB [J].
DE MEIJERE, A ;
MEYER, FE .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) :2379-2411
[9]   Organosulfur compounds: Electrophilic reagents in transition-metal-catalyzed carbon-carbon bond-forming reactions [J].
Dubbaka, SR ;
Vogel, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (47) :7674-7684
[10]   Palladium-catalyzed desulfitative Mizoroki-Heck couplings of sulfonyl chlorides with mono- and disubstituted olefins: Rhodium-catalyzed desulfitative heck-type reactions under phosphine- and base-free conditions [J].
Dubbaka, SR ;
Vogel, P .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (09) :2633-2641