4.7 Article

Rhodium(III)-Catalyzed Direct Cyanation of Aromatic C-H Bond to Form 2-(Alkylamino)benzonitriles Using N-Nitroso As Directing Group

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 24, Pages 12588-12593

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01666

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Funding

  1. National Natural Science Foundation of China [21272117, 21502097]
  2. Priority Academic Program Development of Jiangsu Higher Education Institutions

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2-(Alkylamino)benzonitriles were synthesized via a rhodium-catalyzed cyanation on the aryl C-H bond and subsequent denitrosation of N-nitrosoarylamines using a removable nitroso as the directing group, in which N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) was used as the CN source. Various substituents on the aryl ring and amino group of N-nitrosoarylamines tolerated the reaction, and the corresponding products were achieved in moderate to good yields.

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