A photoexcited halogen-bonded EDA complex of the thiophenolate anion with iodobenzene for C(sp3)-H activation and thiolation.
Chem Sci
; 12(47): 15655-15661, 2021 Dec 08.
Article
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| MEDLINE
| ID: mdl-35003596
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.
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Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Chem Sci
Año:
2021
Tipo del documento:
Article