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Synlett 2010(15): 2263-2266  
DOI: 10.1055/s-0030-1258039
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Unexpected Reduction of N-Hydroxyphthalimides to Phthalimides - Orthogonal Reduction of Functionalized N-Hydroxyphthalimides

Jérôme Jacq, Florian Berthiol*, Cathy Einhorn, Jacques Einhorn*
Département de Chimie Moléculaire (SERCO), UMR-5250, ICMG FR-2607, Université Joseph Fourier, 301 Rue de la Chimie, BP 53, 38041 Grenoble Cedex 9, France
Fax: +33(4)76514836; e-Mail: Jacques.Einhorn@ujf-grenoble.fr;
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Publication History

Received 17 June 2010
Publication Date:
12 August 2010 (online)

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Abstract

A chemoselective reduction of N-hydroxyphthalimides to phthalimides under mild conditions has been discovered. It involves reaction of an N-hydroxyimide with bis(pinacolato)diboron in the presence of a base. Other easily reducible functional groups, such as iodo, nitro, or azido groups are unaffected. Alternatively, such functional groups may be selectively reduced without affecting the N-hydroxyimide moiety using a set of classical conditions.

Key words

chemoselective reduction - bis(pinacolato)diboron - N-hydroxyphthalimides - phthalimides - mild conditions

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