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Iron‐Sulfate‐Catalyzed Direct Dehydrogenative Coupling Cyanation of Secondary Phenylamines
Author(s) -
Huang Mingming,
Deng Qingfu,
Gao Qin,
Shi Jian,
Zhang Xiaohui,
Xiong Yan
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700524
Subject(s) - cyanation , chemistry , iminium , trimethylsilyl cyanide , catalysis , cyanide , electron transfer , combinatorial chemistry , organic chemistry
A direct dehydrogenative coupling cyanation of secondary phenylamines was developed under iron sulfate catalysis by utilizing trimethylsilyl cyanide as a cyano source and tert ‐butyl hydroperoxide as oxidant. A variety of α‐aminonitriles, which commonly serve as versatile synthetically important intermediates, were synthesized in isolated yields of up to 90 %. Based on control experiments, the cyanation mechanism might involve a single‐electron transfer and a subsequent formation of an iminium ion.