Regio- and stereochemical aspects of the palladium-catalyzed desilylation-arylation of substituted vinylsilanes

被引：33

作者：

Alvisi, D

Blart, E

Bonini, BF

Mazzanti, G

Ricci, A

Zani, P

机构：

[1] FAC SCI & TECH,SYNTH ORGAN LAB,F-44072 NANTES 03,FRANCE

[2] FAC CHIM IND,DIPARTIMENTO CHIM ORGAN A MANGINI,I-40136 BOLOGNA,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 20期

关键词：

D O I：

10.1021/jo960301k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed desilylation-arylation of substituted vinylsilanes by p-iodoanisole in the presence of bidentate phosphine ligands is described. Apart from enhancing the rate of the reaction considerably, heteroatom-based functional groups in the vinylsilane moiety have a profound influence on the regiochemistry. A catalytic cycle for the chelation-controlled desilylation-arylation reaction involving five- and six-membered chelate rings is proposed.

引用

页码：7139 / 7146

页数：8

共 36 条

[1] ALPHA-REGIOSELECTIVITY IN PALLADIUM-CATALYZED ARYLATION OF ACYCLIC ENOL ETHERS
CABRI, W
CANDIANI, I
BEDESCHI, A
PENCO, S
SANTI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) : 1481 - 1486
[2] PALLADIUM-CATALYZED ARYLATION OF UNSYMMETRICAL OLEFINS - BIDENTATE PHOSPHINE LIGAND CONTROLLED REGIOSELECTIVITY
CABRI, W
CANDIANI, I
BEDESCHI, A
SANTI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) : 3558 - 3563
[3] PALLADIUM-CATALYZED CONJUGATE ADDITION TYPE REACTION OF ARYL IODIDES WITH ALPHA,BETA-UNSATURATED KETONES
CACCHI, S
ARCADI, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23) : 4236 - 4240
[4] SILYLCUPRATION-MEDIATED SYNTHESIS OF 2-SUBSTITUTED ALLYLAMINES
CAPELLA, L
DEGL'INNOCENTI, A
REGINATO, G
RICCI, A
TADDEI, M
SECONI, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) : 1473 - 1476
[5] SILYLCUPRATION OF N-PHENYL-N-ETHYNYL-ANILINE - A VERSATILE ROUTE TO FUNCTIONALIZED N,N-BIS(PHENYL)ENAMINES
CAPELLA, L
CAPPERUCCI, A
CUROTTO, G
LAZZARI, D
DEMBECH, P
REGINATO, G
RICCI, A
[J]. TETRAHEDRON LETTERS, 1993, 34 (20) : 3311 - 3314
[6] CASARINI A, 1992, SYNLETT, P981
[7] CHAN TH, 1979, SYNTHESIS-STUTTGART, P761
[8] Colvin E. W., 1981, SILICON ORGANIC SYNT, P165
[9] CRETON I, 1994, TETRAHEDRON LETT, V35, P6973
[10] Davies S.G., 1982, ORGANOTRANSITION MET

← 1 2 3 4 →