Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Hypervalent Iodine(III)-Promoted Phenyl Transfer Reaction from Phenyl Hydrazides to Nitriles

Hypervalent Iodine(III)-Promoted Phenyl Transfer Reaction from Phenyl Hydrazides to Nitriles
Nana Ma, Yameng Wan, Zhiguo Zhang, Yan Yan, Qingfeng Liu, Guisheng Zhang
A useful transformation of nitriles to N-phenyl amides has been achieved through a novel intermolecular phenyl transfer reaction from phenyl hydrazides and N-addition to nitriles in the presence of PIFA under mild and solvent-free conditions. This cross-coupling reaction includes the oxidative cleavage of sp2 C–N bonds of phenyl hydrazides to form a phenyl radical and the subsequent N-addition to cyanos to form new sp2 C–N bonds and provides efficient access to various N-phenyl amides in moderate to good yields under mild reaction conditions.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01215

DOI: 10.1021/acs.joc.7b01215

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