Copper-Catalyzed Direct Nitration on Aryl C-H Bonds by Concomitant Azidation-Oxidation with TMS Azide and TBHP under Aerobic Conditions

Botla Vinayak; Malapaka Chandrasekharam

doi:10.1021/acs.orglett.7b01489

Copper-Catalyzed Direct Nitration on Aryl C-H Bonds by Concomitant Azidation-Oxidation with TMS Azide and TBHP under Aerobic Conditions

Org Lett. 2017 Jul 7;19(13):3528-3531. doi: 10.1021/acs.orglett.7b01489. Epub 2017 Jun 21.

Authors

Botla Vinayak¹, Malapaka Chandrasekharam¹

Affiliation

¹ I&PC Division, CSIR-Indian Institute of Chemical Technology , Hyderabad, India.

PMID: 28636391
DOI: 10.1021/acs.orglett.7b01489

Abstract

An unprecedented copper-catalyzed in situ azidation-oxidation for the nitration of anilides and sulfonamides has been developed by direct C_Ar-H functionalization. This novel and efficient nitration protocol is achieved employing TMSN₃ and TBHP without the exclusion of air or moisture. The synthetic applications of the 2-nitroanilides have been explored.

Publication types

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