Catalytic Staudinger Reduction at Room Temperature.

J Org Chem

Institute for Molecules and Materials , Radboud University, Heyendaalseweg 135 , Nijmegen 6525 AJ , The Netherlands.

Published: May 2019

We report an efficient catalytic Staudinger reduction at room temperature that enables the preparation of a structurally diverse set of amines from azides in excellent yields. The reaction is based on the use of catalytic amounts of triphenylphosphine as a phosphine source and diphenyldisiloxane as a reducing agent. Our catalytic Staudinger reduction exhibits a high chemoselectivity, as exemplified by reduction of azides over other common functionalities, including nitriles, alkenes, alkynes, esters, and ketones.

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http://dx.doi.org/10.1021/acs.joc.9b00831DOI Listing

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