Cu/Nitroxyl Catalyzed Aerobic Oxidation of Primary Amines into Nitriles at Room Temperature

Jinho Kim; Shannon S Stahl

doi:10.1021/cs400360e

Cu/Nitroxyl Catalyzed Aerobic Oxidation of Primary Amines into Nitriles at Room Temperature

ACS Catal. 2013 Jul 5;3(7):1652-1656. doi: 10.1021/cs400360e.

Authors

Jinho Kim¹, Shannon S Stahl

Affiliation

¹ Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.

Abstract

An efficient catalytic method has been developed for aerobic oxidation of primary amines to the corresponding nitriles. The reactions proceed at room temperature and employ a catalyst consisting of (4,4'- ^t Bu₂bpy)CuI/ABNO (ABNO = 9-azabicyclo[3.3.1]nonan-3-one N-oxyl). The reactions exhibit excellent functional group compatibility and substrate scope, and are effective with benzylic, allylic and aliphatic amines. Preliminary mechanistic studies suggest that aerobic oxidation of the Cu catalyst is the turnover-limiting step of the reaction.

Keywords: aerobic oxidation; amine oxidation; copper; nitrile; nitroxyl.

Grants and funding

R01 GM100143/GM/NIGMS NIH HHS/United States