Silver(I)-catalysed protiodesilylation of 1-(trimethylsilyl)-1-alkynes

被引：47

作者：

Carpita, A ^{[1
]}

Mannocci, L ^{[1
]}

Rossi, R ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 09期

关键词：

alkynes; silicon; chemoselectivity; protecting groups; silver;

D O I：

10.1002/ejoc.200400810

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A procedure for protiodesilylation of 1-(trimethylsilyl)-1-alkynes that involves the use of catalytic amounts of AgNO3 and does not require the employment of KCN is described. This procedure allows for chemoselective deprotection of 1-(trimethylsilyl)-1-alkynes containing alpha-(trimethylsilyl)benzyl moieties, tert-butyldiphenylsilyl alkyl ethers or tert-butyldimethylsityl aryl ether groups. However, it causes complete desilylation of 1-(trimethylsilyl)-1-alkynes characterised by a primary alcoholic group protected as a tert-butyldimethylsilyl ether, Interestingly, compounds that contain this last functional group can also furnish the corresponding alcohols by treatment a catalytic amount of aqueous HNO3. (c) Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1859 / 1864

页数：6

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