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Palladium/norbornene-catalyzed distal alkenyl C-H arylation and alkylation of cis-olefins.

ABSTRACT: In this full article, a detailed study of a distal alkenyl C-H arylation and alkylation through the palladium/norbornene (NBE) cooperative catalysis is described. Both aminopyridine- and oxime ether-type directing groups have been found effective for this transformation, allowing functionalization of diverse allyl amines and homoallyl alcohols. In addition, the C5,C6-substititued NBEs show optimal reactivity and selectivity. Various cis-olefins can be transformed to the corresponding arylated or alkylated trisubstituted alkenes with excellent regio- and stereoselectivity. Preliminary mechanistic studies support the Catellani pathway instead of the Heck pathway.

SUBMITTER: Wu Z

PROVIDER: S-EPMC8530197 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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Palladium/norbornene-catalyzed distal alkenyl C-H arylation and alkylation of cis-olefins.

Wu Zhao Z Fatuzzo Nina N Dong Guangbin G

Tetrahedron 20210511

In this full article, a detailed study of a distal alkenyl C-H arylation and alkylation through the palladium/norbornene (NBE) cooperative catalysis is described. Both aminopyridine- and oxime ether-type directing groups have been found effective for this transformation, allowing functionalization of diverse allyl amines and homoallyl alcohols. In addition, the C5,C6-substititued NBEs show optimal reactivity and selectivity. Various cis-olefins can be transformed to the corresponding arylated or ...[more]

PMID: 34690377

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