A straightforward route to polyenylsilanes by palladium- or nickel-catalyzed cross-coupling reactions

被引：51

作者：

Babudri, F ^{[1
]}

Farinola, GM ^{[1
]}

Fiandanese, V ^{[1
]}

Mazzone, L ^{[1
]}

Naso, F ^{[1
]}

机构：

[1] Univ Bari, Dipartmento Chim, CNR, Ctr Studio Metodol Innovat Sintesi Organ, I-70126 Bari, Italy

来源：

TETRAHEDRON | 1998年 / 54卷 / 07期

关键词：

D O I：

10.1016/S0040-4020(97)10209-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient conversion of bis-silylated dienes and trienes into polyenylsilanes by cross-coupling reactions is described. The aryl substituted polyenes are synthesized by ipso-borodesilylation with BCl4 followed by Pd-catalyzed coupling reactions of the resulting boron derivative with aryl halides, whereas the synthesis of alkyl substituted polyenes requires the conversion of the boron intermediate into iodo-derivative and the subsequent coupling with alkyl Grignard reagents in the presence of a Ni(II) catalyst. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1085 / 1094

页数：10

共 31 条

[1] PALLADIUM-CATALYZED DIASTEREOSELECTIVE SYNTHESES OF (E)-1-TRIMETHYLSILYL-2-ALKENES, (E)-1-TRIMETHYLSILYL-1-ALKEN-3-YNES, (1E,5E)-1-TRIMETHYLSILYL-1,5-ALKADIEN-3-YNES, (1E,3Z)- AND (1E,3E)-1-TRIMETHYLSILYL-1,3-ALKADIENES
ANDREINI, BP
CARPITA, A
ROSSI, R
SCAMUZZI, B
[J]. TETRAHEDRON, 1989, 45 (17) : 5621 - 5640
[2] A NEW STRAIGHTFORWARD AND GENERAL-APPROACH TO DIENAMIDE NATURAL-PRODUCTS
BABUDRI, F
FIANDANESE, V
NASO, F
PUNZI, A
[J]. TETRAHEDRON LETTERS, 1994, 35 (13) : 2067 - 2070
[3] BABUDRI F, 1995, SYNLETT, P817
[4] CONJUGATED POLYENE SYNTHESIS VIA DISILYL DERIVATIVES - A DIRECT ACCESS TO OSTOPANIC ACID, A PLANT ANTICANCER AGENT, AND TO (6E)-LTB3 LEUKOTRIENE
BABUDRI, F
FIANDANESE, V
NASO, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) : 6245 - 6248
[5] BABUDRI F, 1992, SYNLETT, P221
[6] A GENERAL-APPROACH TO CONJUGATED (E,E)-DIENES THROUGH SEQUENTIAL COUPLING REACTIONS
BABUDRI, F
FIANDANESE, V
MAZZONE, L
NASO, F
[J]. TETRAHEDRON LETTERS, 1994, 35 (47) : 8847 - 8850
[7] A NEW APPROACH TO SILYLATED KETONES AND DICARBONYL-COMPOUNDS WITH A CONJUGATED (ALL-E) DIENE OR TRIENE STRUCTURE
BABUDRI, F
FIANDANESE, V
MARCHESE, G
NASO, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (04) : 237 - 239
[8] BABUDRI F, 1997, IN PRESS J ORG CHEM, V62
[9] REACTION OF ALKENYLBORONIC ACIDS WITH IODINE UNDER INFLUENCE OF BASE - SIMPLE PROCEDURE FOR STEREOSPECIFIC CONVERSION OF TERMINAL ALKYNES INTO TRANS-1-ALKENYL IODIDES VIA HYDROBORATION
BROWN, HC
HAMAOKA, T
RAVINDRA.N
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (17) : 5786 - 5788
[10] STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED 1,3,5-HEXATRIENES FROM DIALLYLIC SULFONES
CAO, XP
CHAN, TL
CHOW, HF
TU, JG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (12) : 1297 - 1299

← 1 2 3 4 →