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Distal Alkenyl C-H Functionalization via the Palladium/Norbornene Cooperative Catalysis.


ABSTRACT: A distal-selective alkenyl C-H arylation method is reported through a directed palladium/norbornene (Pd/NBE) cooperative catalysis. The key is to use an appropriate combination of the directing group and the NBE cocatalyst. A range of acyclic and cyclic cis-olefins are suitable substrates, and the reaction is operated under air with excellent site-selectivity. Preliminary mechanistic studies are consistent with the proposed Pd/NBE-catalyzed C-H activation instead of the Heck pathway. Initial success on distal alkylation has also been achieved using MeI and methyl bromoacetate as electrophiles.

SUBMITTER: Wu Z 

PROVIDER: S-EPMC7075342 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Distal Alkenyl C-H Functionalization via the Palladium/Norbornene Cooperative Catalysis.

Wu Zhao Z   Fatuzzo Nina N   Dong Guangbin G  

Journal of the American Chemical Society 20200203 6


A distal-selective alkenyl C-H arylation method is reported through a directed palladium/norbornene (Pd/NBE) cooperative catalysis. The key is to use an appropriate combination of the directing group and the NBE cocatalyst. A range of acyclic and cyclic <i>cis</i>-olefins are suitable substrates, and the reaction is operated under air with excellent site-selectivity. Preliminary mechanistic studies are consistent with the proposed Pd/NBE-catalyzed C-H activation instead of the Heck pathway. Init  ...[more]

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