Preparation and reaction of 2-aryl-3-silyl-1 3-butadiene

被引：26

作者：

Ikeda, Z ^{[1
]}

Oshima, K ^{[1
]}

Matsubara, S ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo, Kyoto 6158510, Japan

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 22期

关键词：

D O I：

10.1021/ol051557s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A conjugated pi-electron compound, 2-aryl-3-silyi-1,3-butadiene, was easily prepared from 1-benzyloxy-3-sityl-2-propyne, bis(lodozincio)methane, and an aryl halide in the presence of nickel catalyst. A subsequent cross-coupling reaction of the product with another aryl halide gave an unsymmetrical 2,3-diaryl-1,3-butadiene efficiently.

引用

页码：4859 / 4861

页数：3

共 27 条

[1] A straightforward route to polyenylsilanes by palladium- or nickel-catalyzed cross-coupling reactions [J].

Babudri, F ;

Farinola, GM ;

Fiandanese, V ;

Mazzone, L ;

Naso, F .

TETRAHEDRON, 1998, 54 (07) :1085-1094

[2] Sequential cross-coupling of 1,4-bissilylbutadienes: Synthesis of unsymmetrical 1,4-disubstituted 1,3-butadienes [J].

Denmark, SE ;

Tymonko, SA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) :8004-8005

[3] Preparation of enolate-homoenolate species as (Z)-γ-siloxyallylmetal equivalents:: Sequential 1,4-addition of bis(iodozincio)methane to 1,4-dicarbonylbutenes and cyclopropanation [J].

Hirayama, T ;

Oshima, K ;

Matsubara, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (21) :3293-3296

[4] PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF ORGANOMETALLOIDS THROUGH ACTIVATION WITH FLUORIDE-ION [J].

HIYAMA, T ;

HATANAKA, Y .

PURE AND APPLIED CHEMISTRY, 1994, 66 (07) :1471-1478

[5]

Hopf H, 2001, ANGEW CHEM INT EDIT, V40, P705, DOI 10.1002/1521-3773(20010216)40:4<705::AID-ANIE7050>3.3.CO

[6]

2-#

[7] Sequential assembly strategy for tetrasubstituted olefin synthesis using vinyl 2-pyrimidyl sulfide as a platform [J].

Itami, K ;

Mineno, M ;

Muraoka, N ;

Yoshida, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) :11778-11779

[8] Nickel-catalyzed addition of dimethylzinc to aldehydes across alkynes and 1,3-butadiene: An efficient four-component connection reaction [J].

Kimura, M ;

Ezoe, A ;

Mori, M ;

Tamaru, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :201-209

[9] Structure of bis(iodozincio)methane in THF solution [J].

Matsubara, S ;

Oshima, K ;

Matsuoka, H ;

Matsumoto, K ;

Ishikawa, K ;

Matsubara, E .

CHEMISTRY LETTERS, 2005, 34 (07) :952-953

[10] Bis(iodozincio)methane as a synthetic tool [J].

Matsubara, S ;

Oshima, K .

PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES, 2003, 79 (03) :71-77

← 1 2 3 →