ICl/AgNO3 Co-Catalyzed Radical Oxidation of Diaryl- and Alkylarylalkynes into 1,2-Diketones

Wen Yang; Yu Chen; Yongqi Yao; Xin Yang; Qifu Lin; Dingqiao Yang

doi:10.1021/acs.joc.9b01667

ICl/AgNO₃ Co-Catalyzed Radical Oxidation of Diaryl- and Alkylarylalkynes into 1,2-Diketones

J Org Chem. 2019 Sep 6;84(17):11080-11090. doi: 10.1021/acs.joc.9b01667. Epub 2019 Aug 12.

Authors

Wen Yang¹, Yu Chen^{2

3}, Yongqi Yao¹, Xin Yang¹, Qifu Lin¹, Dingqiao Yang¹

Affiliations

¹ Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment , South China Normal University , Guangzhou 510006 , People's Republic of China.
² Department of Chemistry and Biochemistry , Queens College of the City University of New York , 65-30 Kissena Blvd. , Queens , New York 11367 , United States.
³ Ph.D. Program in Chemistry , The Graduate Center of the City University of New York , 365 Fifth Avenue , New York , New York 10016 , United States.

PMID: 31403797
DOI: 10.1021/acs.joc.9b01667

Abstract

A novel ICl/AgNO₃ co-catalyzed radical oxidation of diaryl- and alkylarylalkynes into 1,2-diketones is reported. The reaction proceeded smoothly under mild conditions and generated 1,2-diketones in moderate to good yields with a good tolerance of functional groups. Furthermore, the obtained C4-(1,2-diketoaryl)isoxazoles could react smoothly with 1,2-diaminobenzene to form C4-(3-arylquinoxalin-2-yl)isoxazoles. At last, a new one-pot strategy for the synthesis of quinoxalines from 1,2-diphenylethynes and 1,2-diaminobenzene is also reported.

Publication types

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