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Silver( I )‐Catalysed Protiodesilylation of 1‐(Trimethylsilyl)‐1‐alkynes
Author(s) -
Carpita Adriano,
Mannocci Luca,
Rossi Renzo
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400810
Subject(s) - trimethylsilyl , chemistry , ether , alkyl , aryl , catalysis , organic chemistry , primary (astronomy) , aqueous solution , medicinal chemistry , physics , astronomy
A procedure for protiodesilylation of 1‐(trimethylsilyl)‐1‐alkynes that involves the use of catalytic amounts of AgNO 3 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 HNO 3 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)