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Synthesis 2009(7): 1127-1130  
DOI: 10.1055/s-0028-1087982
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Rapid Chemoselective Deprotection of Benzyl Esters by Nickel Boride

Jitender M. Khurana*, Reema Arora
Department of Chemistry, University of Delhi, Delhi 110007, India
e-Mail: jmkhurana1@yahoo.co.in;
Further Information

Publication History

Received 30 October 2008
Publication Date:
02 March 2009 (online)

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Abstract

Benzyl esters of a variety of acids can be chemoselectively cleaved on treatment with nickel boride in methanol at ambient temperature to give the parent carboxylic acids in high yields. Other protecting functionalities such as methyl, ethyl, tert-butyl, and trityl esters as well as benzyl ethers, tert-butyl ethers, and N-benzylamides are unaffected under these conditions.

Key words

benzyl esters - chemoselectivity - carboxylic acids - cleavage - nickel boride

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