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

Jiawei Dong; Zhongjie Wu; Zhengyi Liu; Ping Liu; Peipei Sun

doi:10.1021/acs.joc.5b01666

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

J Org Chem. 2015 Dec 18;80(24):12588-93. doi: 10.1021/acs.joc.5b01666. Epub 2015 Nov 13.

Authors

Jiawei Dong¹, Zhongjie Wu¹, Zhengyi Liu¹, Ping Liu^{1

2}, Peipei Sun^{1

2}

Affiliations

¹ College of Chemistry and Materials Science, Jiangsu Provincial Key Laboratory of Materials Cycling and Pollution Control, Nanjing Normal University , Nanjing 210097, China.
² Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Nanjing Normal University , Nanjing 210023, China.

PMID: 26539743
DOI: 10.1021/acs.joc.5b01666

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't