title: Metal-Free Oxidation of Primary Amines to Nitriles through Coupled Catalytic Cycles.
abstract: Synergism among several intertwined catalytic cycles allows for selective, room temperature oxidation of primary amines to the corresponding nitriles in 85-98% isolated yield. This metal-free, scalable, operationally simple method employs a catalytic quantity of 4-acetamido-TEMPO (ACT; TEMPO=2,2,6,6-tetramethylpiperidine N-oxide) radical and the inexpensive, environmentally benign triple salt oxone as the terminal oxidant under mild conditions. Simple filtration of the reaction mixture through silica gel affords pure nitrile products.
authors: Department of Chemistry, University of Connecticut, 55 North Eagleville Rd, Storrs, CT, 06269-3060, USA.
authors: Kyle M
authors: KM
authors: Lambert
authors: Department of Chemistry, University of Connecticut, 55 North Eagleville Rd, Storrs, CT, 06269-3060, USA.
authors: James M
authors: JM
authors: Bobbitt
authors: Department of Chemistry, University of Connecticut, 55 North Eagleville Rd, Storrs, CT, 06269-3060, USA.
authors: Sherif A
authors: SA
authors: Eldirany
authors: Department of Chemistry, University of Connecticut, 55 North Eagleville Rd, Storrs, CT, 06269-3060, USA.
authors: Liam E
authors: LE
authors: Kissane
authors: Department of Chemistry, University of Connecticut, 55 North Eagleville Rd, Storrs, CT, 06269-3060, USA.
authors: Rose K
authors: RK
authors: Sheridan
authors: Department of Chemistry, University of Connecticut, 55 North Eagleville Rd, Storrs, CT, 06269-3060, USA.
authors: Zachary D
authors: ZD
authors: Stempel
authors: Department of Chemistry, University of Connecticut, 55 North Eagleville Rd, Storrs, CT, 06269-3060, USA.
authors: Francis H
authors: FH
authors: Sternberg
authors: Department of Chemistry, University of Connecticut, 55 North Eagleville Rd, Storrs, CT, 06269-3060, USA. William.Bailey@uconn.edu.
authors: William F
authors: http://orcid.org/0000-0001-9159-0218
authors: WF
authors: Bailey
keywords: amines; catalysis; nitriles; organic chemistry; synthetic methods