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, Sandip K. Nayak.

Journal Name: Letters in Organic Chemistry

Volume 5 , Issue 6 , 2008

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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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Article Details

VOLUME: 5
ISSUE: 6
Year: 2008
Page: [435 - 443]
Pages: 9
DOI: 10.2174/157017808785740543
Price: $65

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