The palladium-catalyzed cross-coupling reaction of organosilicon compounds with allylic carbonates or diene monoxides

被引:37
作者
Matsuhashi, H
Asai, S
Hirabayashi, K
Hatanaka, Y
Mori, A
Hiyama, T
机构
[1] TOKYO INST TECHNOL, RESOURCES UTILIZAT RES LAB, MIDORI KU, YOKOHAMA, KANAGAWA 226, JAPAN
[2] SAGAMI CHEM RES CTR, SAGAMIHARA, KANAGAWA 229, JAPAN
关键词
D O I
10.1246/bcsj.70.1943
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The cross-coupling reaction of allylic carbonates with organosilanes was found to proceed without fluoride ion activation under mild conditions by using a coordinatively unsaturated palladium complex as a catalyst. The reaction was assumed to proceed through an allylpalladium alkoxide derived from the allylic carbonate substrate and a palladium(0) species, the alkoxo ligand activating the organosilicon reagent. Likewise, diene monoxides also underwent cross-coupling with alkenyl- and arylfluorosilanes in moderate to high yields.
引用
收藏
页码:1943 / 1952
页数:10
相关论文
共 41 条
[1]  
[Anonymous], 1991, COMPREHENSIVE ORGANI
[2]  
[Anonymous], 1972, Inorg. Synth, DOI DOI 10.1002/9780470132449.CH23
[3]  
CAHIEZ C, 1978, SYNTHESIS-STUTTGART, P528
[4]   ASYMMETRIC NICKEL-CATALYZED CROSS-COUPLING REACTION OF ALLYLIC SUBSTRATES WITH GRIGNARD-REAGENTS [J].
CONSIGLIO, G ;
PICCOLO, O ;
RONCETTI, L ;
MORANDINI, F .
TETRAHEDRON, 1986, 42 (07) :2043-2053
[5]   Conversion of allylic alcohols into allylic nitromethyl compounds via a palladium-catalyzed solvolysis: An enantioselective synthesis of an advanced carbocyclic nucleoside precursor [J].
Deardorff, DR ;
Savin, KA ;
Justman, CJ ;
Karanjawala, ZE ;
Sheppeck, JE ;
Hager, DC ;
Aydin, N .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3616-3622
[6]   PALLADIUM-CATALYZED COUPLING OF VINYL EPOXIDES WITH ORGANOSTANNANES [J].
ECHAVARREN, AM ;
TUETING, DR ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) :4039-4041
[7]   SYNTHESIS OF ALPHA-AMINO-ACIDS USING TRANSITION-METAL CATALYSIS-ALKYLATION OF SCHIFF-BASES DERIVED FROM ALPHA - AMINO-ACID ESTERS (REGIO, STEREO - SELECTIVITY [J].
GENET, JP ;
JUGE, S ;
ACHI, S ;
MALLART, S ;
MONTES, JR ;
LEVIF, G .
TETRAHEDRON, 1988, 44 (17) :5263-5275
[8]  
Godleslcy S., 1991, COMPREHENSIVE ORGANI, V4, P585
[9]   THE ALLYLOXYCARBONYL GROUP FOR ALCOHOL PROTECTION - QUANTITATIVE REMOVAL OR TRANSFORMATION INTO ALLYL PROTECTING GROUP VIA PI-ALLYL COMPLEXES OF PALLADIUM [J].
GUIBE, F ;
SAINTMLEUX, Y .
TETRAHEDRON LETTERS, 1981, 22 (37) :3591-3594
[10]  
HATANAKA Y, 1991, SYNLETT, P845