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Synthesis 2020; 52(18): 2689-2697
DOI: 10.1055/s-0040-1707147
paper
© Georg Thieme Verlag Stuttgart · New York

P(OEt)3-Mediated Formal S–H Insertion: Reductive Couplings of Isatins with Thiols to Generate 3-Sulfenylated Oxindoles

Tiao Huang
a   Key Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China   Email: wmsh@hainnu.edu.cn
,
Li Liu
a   Key Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China   Email: wmsh@hainnu.edu.cn
,
Qinghe Wang
a   Key Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China   Email: wmsh@hainnu.edu.cn
,
Dulin Kong∗
b   School of Pharmaceutical Sciences, Hainan Medical University, Haikou 571199, Hainan Province, P. R. of China   Email: kongdulin@126.com
,
Mingshu Wu  ∗
a   Key Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, Hainan Province, P. R. of China   Email: wmsh@hainnu.edu.cn
› Author AffiliationsThis work was supported by Natural Science Foundation of Hainan Province (2019RC215) and Graduate Innovative Research Project of Hainan Normal University (Hsyx2018-25).
Further Information

Publication History

Received: 14 April 2020

Accepted after revision: 20 May 2020

Publication Date:
10 June 2020 (online)

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Abstract

A new P(OEt)3-mediated formal S–H bond-insertion reaction of isatins into thiols for the synthesis of valuable 3-sulfenylation oxindoles has been developed. This approach takes advantage of the unique reactivity of Kukhtin–Ramirez adducts to allow direct reductive S–H functionalization with commercially available and bench-stable starting materials.

Key words

triethyl phosphite - S–H bond insertion - carbenoids - 3-sulfenylation oxindoles - isatins

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707147. Included are experimental details, characterization of new compounds, crystallographic data, and NMR spectra (PDF).
  • Supporting Information
 

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