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Tailored cobalt-salen complexes enable electrocatalytic intramolecular allylic C-H functionalizations.

ABSTRACT: Oxidative allylic C-H functionalization is a powerful tool to streamline organic synthesis as it minimizes the need for functional group activation and generates alkenyl-substituted products amenable to further chemical modifications. The intramolecular variants can be used to construct functionalized ring structures but remain limited in scope and by their frequent requirement for noble metal catalysts and stoichiometric chemical oxidants. Here we report an oxidant-free, electrocatalytic approach to achieve intramolecular oxidative allylic C-H amination and alkylation by employing tailored cobalt-salen complexes as catalysts. These reactions proceed through a radical mechanism and display broad tolerance of functional groups and alkene substitution patterns, allowing efficient coupling of di-, tri- and even tetrasubstituted alkenes with N- and C-nucleophiles to furnish high-value heterocyclic and carbocyclic structures.

SUBMITTER: Cai CY

PROVIDER: S-EPMC8213807 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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Tailored cobalt-salen complexes enable electrocatalytic intramolecular allylic C-H functionalizations.

Cai Chen-Yan CY Wu Zheng-Jian ZJ Liu Ji-Ying JY Chen Ming M Song Jinshuai J Xu Hai-Chao HC

Nature communications 20210618 1

Oxidative allylic C-H functionalization is a powerful tool to streamline organic synthesis as it minimizes the need for functional group activation and generates alkenyl-substituted products amenable to further chemical modifications. The intramolecular variants can be used to construct functionalized ring structures but remain limited in scope and by their frequent requirement for noble metal catalysts and stoichiometric chemical oxidants. Here we report an oxidant-free, electrocatalytic approa ...[more]

PMID: 34145285

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