Synthesis of Carbamoyl Azides from Redox-Active Esters and TMSN3

Author:

Li Yajun1,Bao Hongli1ORCID,Yuan Xiaobin21,Qu Yanjie21

Affiliation:

1. Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Chinese Academy of Sciences

2. College of Chemistry and Materials Science, Fujian Normal University

Abstract

AbstractAn efficient method for construction of C–N bonds is reported here. The iron-catalyzed azidation of N-hydroxy phthalimide (NHP) esters provides a convenient approach for the synthesis of carbamoyl azides with good substrate scope and functional group tolerance. Both aryl carbon C(sp2) and alkyl carbon C(sp3) sources can be used deliver the carbamoyl azides. Mechanistic studies were conducted and a two-stage process was identified.

Funder

National Natural Science Foundation of China

National Key Research and Development Program of China

Chinese Academy of Sciences

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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