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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

CuBr2 Catalyzed One-Pot Transprotection of TBDMS Ethers to Acetates/benzoates: Chemoselective Acetylation of Aliphatic in the Presence of Aromatic TBDMS Ethers

Author(s): Suchitra Bhatt and Sandip K. Nayak

Volume 5, Issue 6, 2008

Page: [435 - 443] Pages: 9

DOI: 10.2174/157017808785740543

Price: $65

Abstract

A variety of TBDMS ethers were directly transprotected into their acetates/benzoates with acetyl chloride/ benzoyl chloride in a one-pot procedure using CuBr2 (30 mol%). Chemo-selective transprotection of aliphatic TBDMS ethers in the presence of aromatic TBDMS ethers was achieved using 10 mol% of the catalyst. Various sensitive functional groups such as ketals, ketones, alkenes, allyl and benzyl ethers were found to be compatible under the reaction conditions.

Keywords: TBDMS ethers, copper(II) bromide, transprotection, acetates, benzoates, chemoselectivity


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