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Rapid Chemoselective Deprotection of Benzyl Esters by Nickel Boride

Jitender M. Khurana*, Reema Arora

*Department of Chemistry, University of Delhi, Delhi 110007, India, Email:

J. M. Khurana, R. Arora, Synthesis, 2009, 1127-1130.

DOI: 10.1055/s-0028-1087982


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

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Key Words

benzyl esters, chemoselectivity, carboxylic acids, cleavage, nickel boride, sodium borohydride

ID: J66-Y2009-1060