4.6 Article

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

Journal

ARABIAN JOURNAL OF CHEMISTRY
Volume 15, Issue 7, Pages -

Publisher

ELSEVIER
DOI: 10.1016/j.arabjc.2022.103896

Keywords

L-cysteine; Sulfur source; C-S coupling; Diaryl sulfide; Heteroarenethiol

Funding

  1. Natural Science Foundation of Liaoning Province of China [2019-ZD-0453, 2020 MS 105]
  2. Fundamental Research Funds for the Central Universities [DUT20LK20]
  3. Career Devel-opment Support Plan for Young and Middle-aged Teachers in Shenyang Pharmaceutical University [ZQN2021007]

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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.
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.

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