Synlett

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

J Jacq, F Berthiol, C Einhorn, J Einhorn

Index: Jacq, Jerome; Berthiol, Florian; Einhorn, Cathy; Einhorn, Jacques Synlett, 2010 , # 15 p. 2263 - 2266

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Citation Number: 2

Abstract

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 ...

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