Nickel Metallaphotoredox Catalysis Enabling Desulfurative Cross Coupling Reactions

Metallaphotoredox processes have emerged as powerful methods for C−C bond formations. The Ni‐photoredox catalyzed desulfurative cross‐coupling of thiol derivatives with aryl bromides has now been established. This procedure provides access to simple and complex unsymmetrical diarylmethane molecules...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2022-12, Vol.364 (24), p.4249-4254
Main Authors: Geniller, Lilian, Taillefer, Marc, Jaroschik, Florian, Prieto, Alexis
Format: Article
Language:English
Subjects:
Bromides
Catalysis
Chemical reactions
Chemical Sciences
Coupling (molecular)
Cross coupling
Functional groups
Nickel
Organic chemistry
Photoredox
Photoredox catalysis
Radicals
Substitution reactions
Thiols
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Summary:Metallaphotoredox processes have emerged as powerful methods for C−C bond formations. The Ni‐photoredox catalyzed desulfurative cross‐coupling of thiol derivatives with aryl bromides has now been established. This procedure provides access to simple and complex unsymmetrical diarylmethane molecules under mild reaction conditions with a broad functional group tolerance. The key steps of the reaction involve a silane‐mediated halogen‐atom transfer (XAT) and a subsequent intramolecular homolytic substitution (SH), forming C‐centered radicals from various thiol derivatives as shown by mechanistic studies. This study paves the way for new transformations of abundant, naturally occurring thiols.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202201152