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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.

SUBMITTER: Li T

PROVIDER: S-EPMC8654056 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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

Li Tao T Liang Kangjiang K Tang Jiaying J Ding Yuzhen Y Tong Xiaogang X Xia Chengfeng C

Chemical science 20211021 47

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(sp<su ...[more]

PMID: 35003596

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