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Aryne-Enabled C-N Arylation of Anilines.

ABSTRACT: Anilines are potentially high-value arylating agents, but are limited by the low reactivity of the strong C-N bond. We show that the reactive intermediate benzyne can be used to both activate anilines, and set-up an aryl transfer reaction in a single step. The reaction does not require any transition metal catalysts or stoichiometric organometallics, and establishes a metal-free route to valuable biaryl products by functionalizing the aniline C-N bond.

SUBMITTER: Sephton T

PROVIDER: S-EPMC10952162 | biostudies-literature | 2023 Dec

REPOSITORIES: biostudies-literature

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Aryne-Enabled C-N Arylation of Anilines.

Sephton Thomas T Charitou Anastasios A Trujillo Cristina C Large Jonathan M JM Butterworth Sam S Greaney Michael F MF

Angewandte Chemie (International ed. in English) 20231106 49

Anilines are potentially high-value arylating agents, but are limited by the low reactivity of the strong C-N bond. We show that the reactive intermediate benzyne can be used to both activate anilines, and set-up an aryl transfer reaction in a single step. The reaction does not require any transition metal catalysts or stoichiometric organometallics, and establishes a metal-free route to valuable biaryl products by functionalizing the aniline C-N bond. ...[more]

PMID: 37850515

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