Syntheses of N-Alkyl 2-Arylindoles from Saturated Ketones and 2-Arylethynylanilines via Cu-Catalyzed Sequential Dehydrogenation/Aza-Michael Addition/Annulation Cascade

Fei Ling; Dingguo Song; Linlin Chen; Tao Liu; Mengyao Yu; Yan Ma; Lian Xiao; Min Xu; Weihui Zhong

doi:10.1021/acs.joc.9b03091

Syntheses of N-Alkyl 2-Arylindoles from Saturated Ketones and 2-Arylethynylanilines via Cu-Catalyzed Sequential Dehydrogenation/Aza-Michael Addition/Annulation Cascade

J Org Chem. 2020 Mar 6;85(5):3224-3233. doi: 10.1021/acs.joc.9b03091. Epub 2020 Feb 14.

Authors

Fei Ling^{1

2}, Dingguo Song¹, Linlin Chen¹, Tao Liu¹, Mengyao Yu¹, Yan Ma², Lian Xiao¹, Min Xu³, Weihui Zhong^{1

2}

Affiliations

¹ Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China.
² Institute of Pharmaceutical Science and Technology, Zhejiang University of Technology, Hangzhou 310014, China.
³ Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China.

PMID: 32013427
DOI: 10.1021/acs.joc.9b03091

Abstract

We describe here a Cu-catalyzed and 4-OH-TEMPO-mediated sequential dehydrogenation/aza-Michael addition/annulation cascade reaction for the construction of N-alkyl 2-arylindoles from facilely available saturated ketones and 2-arylethynylanilines. This reaction shows high regioselectivity and tolerates a variety of functional groups. Moreover, 3-alkyl-substituted indoles can also be achieved when using 2-alkylethynylanilines as starting materials.

Publication types

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