Silver(I)-Catalysed Protiodesilylation of 1-(Trimethylsilyl)-1-alkynes

Adriano Carpita, Luca Mannocci, Renzo Rossi*

*Dipartimento di Chimica e Chimica Industriale, University of Pisa, Via Risorgimento 35, 56126 Pisa, Italy, Email: rossidcci.unipi.it

A. Carpita, L. Mannocci, R. Rossi, Eur. J. Org. Chem., 2005, 1367-1377.

DOI: 10.1002/ejoc.200400810

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Abstract

A procedure for protiodesilylation of 1-(trimethylsilyl)-1-alkynes involves the use of catalytic amounts of AgNO₃. The mechanism and selectivity of this reaction are discussed. In addition, treatment of 1-[(tert-butyldimethylsilyl)oxy]undecane with 10 mol-% of concentrated HNO₃ in presence of 100 eq. water furnished 1-undecanol.

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Key Words

Alkynes, Silicon, Chemoselectivity, Protecting groups, Silver, Desilylations

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ID: J24-Y2005-540