L-cysteine as sustainable and effective sulfur source in the synthesis of diaryl sulfides and heteroarenethiols

L-cysteine, a natural and essential amino acid, was employed as novel sulfur source in the synthesis of symmetrical diaryl sulfides from a variety of aryl iodides in moderate to excellent yields. A tandem three steps' reactions including C(sp2)-S bond formation, C(sp3)-S bond cleavage and another C(sp2)-S bond formation were proposed to be involved in this conversion. This proto-col was featured by broad substrate scope and good functional group tolerance. In addition, heteroarenes including benzothiazoles and benzoxazoles were successfully converted into the corresponding heteroarenethiols using L-cysteine as C-H mercaptalization reagent. (c) 2022 The Author(s). Published by Elsevier B.V. on behalf of King Saud University.

Automated summary

L-cysteine was used as a sulfur source for the synthesis of symmetrical diaryl sulfides with broad substrate scope and good functional group tolerance. Additionally, benzothiazoles and benzoxazoles were successfully converted into heteroarenethiols using L-cysteine as a C-H mercaptalization reagent.