Metal‐Free Oxidation of Primary Amines to Nitriles through Coupled Catalytic Cycles. Issue 15 (22nd February 2016)

• Record Type: Journal Article
• Authors: Lambert, Kyle M.; Bobbitt, James M.; Eldirany, Sherif A.; Kissane, Liam E.; Sheridan, Rose K.; Stempel, Zachary D.; Sternberg, Francis H.; Bailey, William F.
• Is Part Of: Chemistry. Volume 22:Issue 15(2016)
• Page Start: 5156
• Page End: 5159
• Publication Date: 2016-02-22
• Subjects: amines -- catalysis -- nitriles -- organic chemistry -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201600549
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : Synergistic cooperation ! Several intertwined catalytic cycles allow 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) radical and the inexpensive, environmentally benign triple salt oxone as the terminal oxidant under mild conditions (see scheme; TEMPO=2, 2, 6, 6‐tetramethylpiperidine N ‐oxide).