Copper-Catalyzed C5-H Sulfenylation of Unprotected 8-Aminoquinolines Using Sulfonyl Hydrazides

Qing Yu; Yiming Yang; Jie-Ping Wan; Yunyun Liu

doi:10.1021/acs.joc.8b01658

Copper-Catalyzed C5-H Sulfenylation of Unprotected 8-Aminoquinolines Using Sulfonyl Hydrazides

J Org Chem. 2018 Sep 21;83(18):11385-11391. doi: 10.1021/acs.joc.8b01658. Epub 2018 Aug 20.

Authors

Qing Yu¹, Yiming Yang¹, Jie-Ping Wan¹, Yunyun Liu¹

Affiliation

¹ College of Chemistry and Chemical Engineering , Jiangxi Normal University , Nanchang 330022 , P.R. China.

PMID: 30079729
DOI: 10.1021/acs.joc.8b01658

Abstract

The synthesis of C5-sulfenylated 8-aminoquinolines using unprotected 8-aminoquinolines and sulfonyl hydrazides is achieved via the catalysis of CuI. The reactions are hypothesized to proceed via the Cu(I)-Cu(II)-Cu(I) catalytic processes induced by aerobic oxidation and single-electron transfer on the Cu(II)-8-aminoquinoline complex. This work discloses an unprecedented step-efficient method for the synthesis of C5-sulfenylated 8-aminoquinolines bearing a useful free NH₂ group.