Sodium Iodide (NaI)-Catalyzed Cross-Coupling for C-S Bond Formation via Oxidative Dehydrogenation: Cheap, Direct Access to Unsymmetrical Aryl Sulfides

Chem Asian J. 2017 Oct 18;12(20):2675-2679. doi: 10.1002/asia.201701163. Epub 2017 Oct 10.

Abstract

A simple and practical NaI-catalyzed direct C-H sulfenylation of arenes has been developed under air. In this reaction, aryl sulfides were obtained in moderate to excellent yields with high regioselectivity from readily available aromatic compounds and aryl/alkyl thiols, even on gram scale. To demonstrate the practicability of this reaction, two bioactive compound skeletons were synthesized in good yields. This method can also be used to late-stage modification of curcumin.

Keywords: C−H sulfenylation; aryl sulfides; cross-coupling; regioselectivity; sodium iodide.