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 α-(trimethylsilyl)benzyl moieties, tert-butyldiphenylsilyl alkyl ethers or tert-butyldimethylsilyl 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 with a catalytic amount of aqueous HNO3.

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

CARPITA, ADRIANO;ROSSI, RENZO
2005

Abstract

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 α-(trimethylsilyl)benzyl moieties, tert-butyldiphenylsilyl alkyl ethers or tert-butyldimethylsilyl 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 with a catalytic amount of aqueous HNO3.
Carpita, Adriano; Mannocci, L; Rossi, Renzo
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/206300
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