Alkene Hydrobenzylation by a Single Catalyst That Mediates Iterative Outer-Sphere Steps

Cross-coupling catalysts typically react and unite functionally distinct partners via sequential inner-sphere elementary steps: coordination, migratory insertion, reductive elimination, etc. Here, we report a single catalyst that cross-couples styrenes and benzyl bromides via iterative outer-sphere...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 146; no. 4; pp. 2351 - 2357
Main Authors Kong, Lingran, Gan, Xu-cheng, van der Puyl Lovett, Vincent A., Shenvi, Ryan A.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 31.01.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ACTIVATION
IRON(III) PORPHYRINS
MECHANISM
COMPLEXES
HYDRIDE EXPULSION
OLEFINS
TRANSITION-STATE
ASYMMETRIC HYDROGENATION
ORGANOSILICON CHEMISTRY
CENTER-DOT TRANSFER
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Summary:Cross-coupling catalysts typically react and unite functionally distinct partners via sequential inner-sphere elementary steps: coordination, migratory insertion, reductive elimination, etc. Here, we report a single catalyst that cross-couples styrenes and benzyl bromides via iterative outer-sphere steps: metal–ligand-carbon interactions. Each partner forms a stabilized radical intermediate, yet heterocoupled products predominate. The system is redox-neutral and, thus, avoids exogenous oxidants, resulting in simple and scalable conditions. Numerous variations of alkene hydrobenzylation are made possible, including access to the privileged heterodibenzyl (1,2-diarylethane) motif and challenging quaternary carbon variants.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.3c13398