Meta-Dehydrogenative Alkylation of Arenes with Ethers, Ketones, and Esters Catalyzed by Ruthenium

Gang Li; Yuan Gao; Chunqi Jia; Shichong Wang; Bingxu Yan; Yu Fang; Suling Yang

doi:10.1021/acs.orglett.0c02698

Meta-Dehydrogenative Alkylation of Arenes with Ethers, Ketones, and Esters Catalyzed by Ruthenium

Org Lett. 2020 Nov 20;22(22):8758-8763. doi: 10.1021/acs.orglett.0c02698. Epub 2020 Nov 5.

Authors

Gang Li¹, Yuan Gao¹, Chunqi Jia², Shichong Wang¹, Bingxu Yan¹, Yu Fang¹, Suling Yang¹

Affiliations

¹ College of Chemistry and Chemical Engineering, Henan Province Key Laboratory of New Optoelectronic Functional Materials, Anyang Normal University, Anyang 455002, P.R. China.
² Engineering Research Center of Molecular Medicine of Ministry of Education, Key Laboratory of Fujian Molecular Medicine, Key Laboratory of Xiamen Marine and Gene Drugs, School of Biomedical Sciences, Huaqiao University, Xiamen 361021, P.R. China.

PMID: 33151082
DOI: 10.1021/acs.orglett.0c02698

Abstract

A meta-dehydrogenative alkylation of arenes with cyclic ethers, ketones, and esters catalyzed by ruthenium is achieved in the presence of a di-tert-butyl peroxide (DTBP) oxidant. Interestingly, when quinoline and isoquinoline are employed as the directing group, or a chain ether as alkylation reagent, the system produces Minisci reaction products. Mechanistic study indicates that meta-dehydrogenative alkylation is a radical process initiated by DTBP with the assistance of a C_Ar-Ru bond ortho/para-directing effect.