THIOPHENOL PROTECTING GROUPS FOR THE PALLADIUM-CATALYZED HECK REACTION - EFFICIENT SYNTHESES OF CONJUGATED ARYLTHIOLS

被引:66
作者
HSUNG, RP
BABCOCK, JR
CHIDSEY, CED
SITA, LR
机构
[1] UNIV CHICAGO,DEPT CHEM,SEARLE CHEM LAB,CHICAGO,IL 60637
[2] STANFORD UNIV,DEPT CHEM,PALO ALTO,CA 94305
基金
美国国家科学基金会;
关键词
D O I
10.1016/0040-4039(95)00861-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of S-thiophenol protecting groups have been evaluated for the Heck reaction. Of these, the S-acetyl group appears to be the best suited for facile removal under mild conditions to provide the corresponding free thiols in high yields.
引用
收藏
页码:4525 / 4528
页数:4
相关论文
共 14 条
[1]   COADSORPTION OF FERROCENE-TERMINATED AND UNSUBSTITUTED ALKANETHIOLS ON GOLD - ELECTROACTIVE SELF-ASSEMBLED MONOLAYERS [J].
CHIDSEY, CED ;
BERTOZZI, CR ;
PUTVINSKI, TM ;
MUJSCE, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4301-4306
[2]   FREE-ENERGY AND TEMPERATURE-DEPENDENCE OF ELECTRON-TRANSFER AT THE METAL-ELECTROLYTE INTERFACE [J].
CHIDSEY, CED .
SCIENCE, 1991, 251 (4996) :919-922
[3]  
Heck R.F., 1991, COMPREHENSIVE ORGANI, V4, P833, DOI DOI 10.1016/B978-0-08-052349-1.00110-4
[4]  
HECK RF, 1982, ORG REACTIONS, V27, P345
[5]   PALLADIUM(II)-ASSISTED REACTIONS OF MONOOLEFINS [J].
HEGEDUS, LS .
TETRAHEDRON, 1984, 40 (13) :2415-2434
[6]   PALLADIUM-CATALYZED SYNTHESIS OF CINNAMYLAMINES [J].
MALEK, NJ ;
MOORMANN, AE .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (27) :5395-5397
[7]   PALLADIUM-CATALYZED VINYLIC SUBSTITUTION-REACTIONS WITH CARBOXYLIC-ACID DERIVATIVES [J].
PATEL, BA ;
ZIEGLER, CB ;
CORTESE, NA ;
PLEVYAK, JE ;
ZEBOVITZ, TC ;
TERPKO, M ;
HECK, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (24) :3903-3907
[8]   SYNTHESIS OF FERROCENYLACETYLENES [J].
ROSENBLUM, M ;
BRAWN, N ;
PAPENMEIER, J ;
APPLEBAU.M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1966, 6 (02) :173-+
[9]  
SALEN JD, 1987, LANGMUIR, V3, P932
[10]  
SITA LR, UNPUB ORGANOMETALLIC