Copper-Catalyzed Amination of C(sp3)-H bonds: From Anilides to Indolines

Jinguo Long; Liyuan Le; Takanori Iwasaki; Renhua Qiu; Nobuaki Kambe

doi:10.1021/acs.joc.9b02404

Copper-Catalyzed Amination of C(sp³)-H bonds: From Anilides to Indolines

J Org Chem. 2020 Jan 17;85(2):482-492. doi: 10.1021/acs.joc.9b02404. Epub 2019 Dec 13.

Authors

Jinguo Long¹, Liyuan Le¹, Takanori Iwasaki^{2

3}, Renhua Qiu^{1

2}, Nobuaki Kambe^{1

2}

Affiliations

¹ State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering , Hunan University , Changsha 410082 , P.R. China.
² Department of Applied Chemistry, Graduate School of Engineering , Osaka University , Suita, Osaka 565-0871 , Japan.
³ Department of Chemistry and Biotechnology, Graduate School of Engineering , The University of Tokyo , 7-3-1 Hongo , Bunkyoku, Tokyo 113-8656 , Japan.

PMID: 31769677
DOI: 10.1021/acs.joc.9b02404

Abstract

Copper-catalyzed oxidative intramolecular cyclization of o-alkylated anilines via cleavage of C(sp³)-H and N-H bonds for the production of indolines is described. This approach provides a straightforward strategy for the synthesis of nitrogen-containing heterocyclic compounds through the functionalization of unactivated C(sp³)-H bonds with high site selectivity. The present catalytic system shows high preference for functionalization of unactivated C(sp³)-H bonds over C(sp²)-H bonds, leading to C-N bond formation.

Publication types

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