A photoexcited halogen-bonded EDA complex of the thiophenolate anion with iodobenzene for C(sp3)–H activation and thiolation

Abstract

Thiophenol was discovered to form an EDA complex with iodobenzene through halogen bonding interactions upon treatment with KOH. A direct photochemical thiolation of C(sp3)–H bond-containing etheric, allylic, and benzylic substrates with thiophenol was developed. The reaction proceeded on the basis of the in situ generation of a thiyl radical and aryl radical through single electron transfer between the photoexcited thiophenolate anion and aryl iodide EDA complex. Then a C(sp3) centred-radical was formed by aryl radical-mediated hydrogen atom transfer and the thiolation products were delivered via a radical–radical cross-coupling with the thiyl radical.

Graphical abstract: A photoexcited halogen-bonded EDA complex of the thiophenolate anion with iodobenzene for C(sp3)–H activation and thiolation

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Article information

Article type
Edge Article
Submitted
06 Jul 2021
Accepted
20 Oct 2021
First published
21 Oct 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021, Advance Article

A photoexcited halogen-bonded EDA complex of the thiophenolate anion with iodobenzene for C(sp3)–H activation and thiolation

T. Li, K. Liang, J. Tang, Y. Ding, X. Tong and C. Xia, Chem. Sci., 2021, Advance Article , DOI: 10.1039/D1SC03667J

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