Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: An entry to tetraorganosilicon reagents for the silicon-based cross-coupling reaction

被引:185
作者
Nakao, Y [1 ]
Imanaka, H [1 ]
Sahoo, AK [1 ]
Yada, A [1 ]
Hiyama, T [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan
关键词
D O I
10.1021/ja051281j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes, highly stable tetraorganosilicon reagents, are found to react with aryl and alkenyl iodides in the presence of a palladium catalyst and K2CO3 as a base, significantly milder conditions compared with those ever reported for the silicon-based cross-coupling reactions. The reaction tolerates a wide range of functional groups, including silyl protectors, and allows a gram-scale synthesis to recover and reuse the silicon residue. Copyright © 2005 American Chemical Society.
引用
收藏
页码:6952 / 6953
页数:2
相关论文
共 36 条
[1]   Vinyldimethylphenylsilanes as safety catch silanols in fluoride-free palladium-catalyzed cross-coupling reactions [J].
Anderson, JC ;
Munday, RH .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (25) :8971-8974
[2]   A CONVENIENT AND NOVEL ROUTE TO BIS(ETA-ALKYNE)PLATINUM(0) AND OTHER PLATINUM(0) COMPLEXES FROM SPEIER HYDROSILYLATION CATALYST H2[PTCL6].XH2O - X-RAY STRUCTURE OF [PT((ETA-CH2=CHSIME2)2O)(P-TERT-BU3)] [J].
CHANDRA, G ;
LO, PY ;
HITCHCOCK, PB ;
LAPPERT, MF .
ORGANOMETALLICS, 1987, 6 (01) :191-192
[3]   REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES [J].
CHUIT, C ;
CORRIU, RJP ;
REYE, C ;
YOUNG, JC .
CHEMICAL REVIEWS, 1993, 93 (04) :1371-1448
[4]  
Denmark S.E., 2004, Metal-Catalyzed Cross-Coupling Reactions, V1, P163, DOI DOI 10.1002/9783527619535.CH4
[5]   Palladium-catalyzed cross-coupling reactions of substituted aryl(dimethyl)silanols [J].
Denmark, SE ;
Ober, MH .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1703-1714
[6]   Palladium-catalyzed cross-coupling reactions of 2-indolyldimethylsilanois with substituted aryl halides [J].
Denmark, SE ;
Baird, JD .
ORGANIC LETTERS, 2004, 6 (20) :3649-3652
[7]   Cross-coupling reactions of alkenylsilanolates. Investigation of the mechanism and identification of key intermediates through kinetic analysis [J].
Denmark, SE ;
Sweis, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (15) :4876-4882
[8]   Tandem intramolecular silylformylation and silicon-assisted cross-coupling reactions.: Synthesis of geometrically defined α,β-unsaturated aldehydes [J].
Denmark, SE ;
Kobayashi, T .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13) :5153-5159
[9]   Fluoride-free cross-coupling of organosilanols [J].
Denmark, SE ;
Sweis, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (26) :6439-6440
[10]   Highly stereospecific, cross-coupling reactions of alkenylsilacyclobutanes [J].
Denmark, SE ;
Choi, JY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (24) :5821-5822