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.
|Autori:||CARPITA A; MANNOCCI L; ROSSI R|
|Titolo:||Silver(I)-catalysed protiodesylilation of (1-trimethylsilyl)-1-alkynes|
|Anno del prodotto:||2005|
|Digital Object Identifier (DOI):||10.1002/ejoc.200400810|
|Appare nelle tipologie:||1.1 Articolo in rivista|