N-Heterocyclic carbene catalyzed oxidative stannylation of aldehydes: a facile entry to organotin(IV) carboxylates

TitleN-Heterocyclic carbene catalyzed oxidative stannylation of aldehydes: a facile entry to organotin(IV) carboxylates
Publication TypeJournal Article
Year of Publication2013
AuthorsReddi, RN, Malekar, PV, Sudalai, A
JournalTetrahedron Letters
Volume54
Issue21
Pagination2679-2681
Date PublishedMAY
ISSN0040-4039
KeywordsCarboxylic acid stannanes, N-Heterocyclic carbene, Oxidative stannylation, oxygen, Tributyltin chloride
Abstract

A simple protocol is described for the oxidative transformation of aldehydes to the corresponding organotin(IV) carboxylates in high yields (up to 90%) that utilizes atmospheric O-2 as the sole oxidant, N-heterocyclic carbene as catalyst (at 10 mol %), and tributyl tin chloride as stannylating agent. The uniqueness of the reaction lies in the direct conversion of aldehydes to the corresponding organotin(IV) carboxylates via stannylation of carboxylic acids, generated from the reaction of a Breslow intermediate with O-2. (c) 2013 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetlet.2013.03.050
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.391
Divison category: 
Chemical Engineering & Process Development