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Synthesis
DOI: 10.1055/a-2600-4572
paper

Iron-Catalyzed P(O)–S Bond Formation through Cross-Dehydrogenative Coupling of Thiols with P(O)H Compounds

Yuge Ji‡
a   School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China
,
Bing Han‡
a   School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China
,
Hongbin Liu
a   School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China
,
Di Song∗
a   School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China
,
Lei Liu  ∗
a   School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China
b   School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China
c   Shenzhen Research Institute of Shandong University, Shenzhen 518057, P. R. of China
,
Gang Wang∗
a   School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China
› Author Affiliations
This work was financially supported by the National Science Foundation of China (22301164, 22425108, and 82404420), the Natural Science Foundation of Shandong Province (ZR2022QB007, ZR2024MB056, and ZR2023QH409), the Taishan Scholar Project of Shandong Province, and Shenzhen Special Funds (JCYJ20220530141205011).
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Abstract

We herein report an iron(salan)-catalyzed cross-dehydrogenative coupling of thiols with P(O)H compounds for the efficient synthesis of a range of thiophosphates, thiophosphinates, and thiophosphinites. This mild and practical method employs environmentally benign air as terminal oxidant, and earth-abundant metal iron at a low loading as catalyst, and exhibits broad substrate scope and good functional group tolerance, which is applicable to bioactive molecule preparation.

Key words

iron catalysis - P(O)–S bond formation - cross-dehydrogenative coupling - thiophosphates - synthetic methods

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2600-4572.
  • Supporting Information


Publication History

Received: 27 March 2025

Accepted after revision: 05 May 2025

Accepted Manuscript online:
05 May 2025

Article published online:
11 June 2025

© 2025. Thieme. All rights reserved

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