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

Tiao Huang; Li Liu; Qinghe Wang; Dulin Kong; Mingshu Wu

doi:10.1055/s-0040-1707147

Synthesis, Table of Contents

Synthesis 2020; 52(18): 2689-2697
DOI: 10.1055/s-0040-1707147

paper

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

Tiao Huang

^aKey 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

^aKey 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

^aKey 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∗

^bSchool of Pharmaceutical Sciences, Hainan Medical University, Haikou 571199, Hainan Province, P. R. of China Email: kongdulin@126.com

,

Mingshu Wu ∗

^aKey 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

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Abstract

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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

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References

References

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