DOI: 10.1021/acs.joc.6c01448 ISSN: 0022-3263
Copper-Catalyzed C–H Sulfonylation with NSAPI Participation under the Assistance of Directing Group
Manyi Chen, Zeyi Wang, Zhangjie Zhou, Xinxin Wang, Pengfei Zhang, Jun XuAbstract
Herein, we describe an efficient ortho C–H sulfonylation of 8-aminoquinoline-tethered benzoic acid derivatives using N-sulfonyl-aminophthalimide (NSAPI) as the sulfonylating source. Mechanistic investigations support a radical process, wherein cleavage of the ortho C(sp2)–H bond is rate-determining. The active copper species is regenerated by atmospheric oxygen, allowing for low catalyst loading and broad substrate/functional group tolerance.