A new selective approach to 1,1-bis(silyl)-2-arylethenes and 1,1-bis(silyl)-1,3-butadienes via sequential silylative coupling-heck coupling reactions

被引：33

作者：

Pawluc, Piotr ^{[1
]}

Hreczycho, Grzegorz ^{[1
]}

Marciniec, Bogdan ^{[1
]}

机构：

[1] Adam Mickiewicz Univ Poznan, Fac Chem, Dept Organomet Chem, PL-60780 Poznan, Poland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 22期

关键词：

D O I：

10.1021/jo0616254

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel selective route to 1,1-bis(silyl)-1-alkenes has been developed. Sequential one-pot silylative coupling exo-cyclization of 1,2-bis(dimethylvinylsiloxy)ethane followed by the reaction with Grignard reagents leads to the desired 1,1-bis(silyl)ethenes, which are then efficiently coupled in the presence of silver nitrate and palladium acetate with aryl or alkenyl idodides to give the corresponding 1,1-bis(silyl)-2-arylethenes or 1,1,4-trisubstituted 1,3-butadienes with high yield.

引用

页码：8676 / 8679

页数：4

共 50 条

[41] 1,1-BIS(DIPHENYLPHOSPHORYL)-2,2,2-TRIFLUOROETHANOL - NEW INTERMEDIATE OF TRIFLUOROACETYLDIPHENYLPHOSPHANE OXIDATION BY MOLECULAR-OXYGEN
LINDNER, E
EBERT, HD
LESIECKI, H
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (01): : 41 - 41
[42] Azolyl derivatives of nitrohalogenbutadienes - Part 1. Reaction of 1,1-bis(benzotriazol-1-yl)-2-nitrotrihalo-1,3-butadienes with N-nucleophilic, N,N-nucleophilic and N,O-nucleophilic reagents
Zapolskii, VA
Potkin, VI
Nechai, NI
Kaberdin, RV
Pevzner, MS
ZHURNAL ORGANICHESKOI KHIMII, 1997, 33 (10): : 1541 - 1547
[43] Studies on Some Bioactive 1,1-Bis(2-benzylidene-5-aryliden-1,3-thiadiazolidin-4-one) cyclopropane
Panwar, Hemant
Chaudhary, Nidhi
Singh, Sachi
Chawla, Amit
JOURNAL OF THE KOREAN CHEMICAL SOCIETY-DAEHAN HWAHAK HOE JEE, 2011, 55 (06): : 994 - 999
[44] A macromonomer approach to the synthesis of poly(1,1-bis(ethoxycarbonyl)-2-vinyl cyclopropane-graft-dimethyl siloxane)
Sarker, Prodip
Rehman, Saif U. R.
Rimmer, Stephen
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2013, 51 (08) : 1822 - 1830
[45] DIMETHOXY AROMATIC-COMPOUNDS .5. NITRATION AND NITRO DEALKYLATION REACTIONS OF 1,1-BIS(DIMETHOXYPHENYL)-2-METHYLPROPANES
NATOLI, MC
CERAULO, L
LAMARTINA, L
GAZZETTA CHIMICA ITALIANA, 1989, 119 (03): : 145 - 152
[46] Synthesis of 3-hydroxy-5-alkoxyhomophthalates by domino '2: 1-coupling/intramolecular aldol condensation' reactions of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with tetraalkoxymethanes
Lubbe, Mathias
Langer, Peter
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (04) : 881 - 885
[47] REACTIONS BETWEEN 3'-METHYL-6-NITROSPIRO[2H-1-BENZOPYRAN-2,2'-BENZOTHIAZOLINES] AND 1,1-BIS[4-(DIMETHYLAMINO)PHENYL]ETHYLENE AND REACTIONS OF SALICYLALDEHYDES WITH 1,1-BIS[4-(DIMETHYLAMINO)PHENYL]PROPENE - STRIKING EFFECT OF AN EXTRA METHYL-GROUP - PHOTOCHROMIC CHROMENES
ZWANENBURG, DJ
MAAS, TAMM
RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1976, 95 (05): : 97 - 101
[48] Synthesis of 2-(arylthio)benzoates by [3+3] cyclocondensations of 3-arylthio-1-silyloxy-1,3-butadienes with 3-oxo-orthoesters, 1,1,3,3-tetramethoxypropane and 1,1-bis(methylthio)-1-en-3-ones
Imran, Muhammad
Iqbal, Inam
Rasool, Nasir
Fischer, Christine
Langer, Peter
TETRAHEDRON, 2009, 65 (43) : 8794 - 8801
[49] Thermolysis of 1,1-dimesityl-3-phenyl-2-trimethylsilyl-1-silacyclopropene: silylene transfer reactions to 1,4-bis(silyl)butadiynes
Kunai, A
Mihara, T
Matsuo, Y
Ohshita, J
Naka, A
Ishikawa, M
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 545 : 611 - 613
[50] Tautomerism in bis(oxazolines): an experimental and theoretical study of proton transfer in 1,1-bis(4,4-dimethyl-1,3-oxazolin-2-yl)-ethane
Milione, Stefano
Bertolasi, Valerio
TETRAHEDRON LETTERS, 2011, 52 (28) : 3570 - 3574

← 1 2 3 4 5 →