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One-Carbon Homologation of Primary Alcohols to Carboxylic Acids, Esters, and Amides via Mitsunobu Reactions with MAC Reagents

Natsuko Kagawa*, Antoinette E. Nibbs and Viresh H. Rawal*

*Chiba University, 1-8-1 Inohana, Chiba 260-8675, Japan; University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, United States, Email: knatsukofaculty.chiba-u.jp, vrawaluchicago.edu

N. Kagawa, A. E. Nibbs, V. H. Rawal, Org. Lett., 2016, 18, 2363-2366.

DOI: 10.1021/acs.orglett.6b00790 (free Supporting Information)


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Abstract

A one-carbon homologation of an alcohol to the extended carboxylic acid, ester, or amide involves a Mitsunobu reaction with an alkoxymalononitrile, followed by unmasking in the presence of a suitable nucleophile. The homologation and unmasking can even be performed in a one-pot process in high yield.

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Key Words

Mitsunobu reaction, carboxylation, hydrolysis, amides, esters


ID: J54-Y2016