Fluoride-ion-mediated reactions of trimethylsilylacetylene with carbonyl compounds and terminal acetylenes

被引：20

作者：

Abele, E ^{[1
]}

Rubina, K ^{[1
]}

Abele, R ^{[1
]}

Popelis, J ^{[1
]}

Mazeika, I ^{[1
]}

Lukevics, E ^{[1
]}

机构：

[1] Latvian Inst Organ Synth, LV-1006 Riga, Latvia

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1999年 / 586卷 / 02期

关键词：

trimethylsilylacetylene; fluoride ion; carbonyl compounds; aryl and hetaryl acetylenes;

D O I：

10.1016/S0022-328X(99)00262-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Fluoride-ion-mediated reaction of trimethylsilylacetylene with carbonyl compounds has been thoroughly studied. The products of addition to the C=O bond were obtained in 15-66% yield, their subsequent silylation and addition to the second molecule of the carbonyl compound being observed. It has been found that terminal aryl and hetaryl acetylenes undergo silylation in a two-phase-system Me3SiC=CH/CsF/18-crown-6 to afford aryl(hetaryl) trimethylsilylacetylenes with up to 100% yields. Combining these two reactions, a novel one-pot fluoride-ion-mediate method for the synthesis of 1-trimethylsiloxy-3-aryl(hetaryl)-2-propynes from trimethylsilylacetylene, terminal aryl or hetaryl acetylenes and carbonyl compounds has been elaborated. (C) 1999 Elsevier Science S.A. All rights reserved.

引用

页码：184 / 189

页数：6

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