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Metal‐Free Oxidation of Primary Amines to Nitriles through Coupled Catalytic Cycles
Author(s) -
Lambert Kyle M.,
Bobbitt James M.,
Eldirany Sherif A.,
Kissane Liam E.,
Sheridan Rose K.,
Stempel Zachary D.,
Sternberg Francis H.,
Bailey William F.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600549
Subject(s) - catalysis , primary (astronomy) , yield (engineering) , nitrile , chemistry , filtration (mathematics) , metal , salt (chemistry) , oxide , combinatorial chemistry , organic chemistry , materials science , physics , statistics , mathematics , astronomy , metallurgy
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.