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Catalytic Strategy for Regioselective Arylethylamine Synthesis.

ABSTRACT: A mild, modular, and practical catalytic system for the synthesis of the highly privileged phenethylamine pharmacophore is reported. Using a unique combination of organic catalysts to promote the transfer of electrons and hydrogen atoms, this system performs direct hydroarylation of vinyl amine derivatives with a wide range of aryl halides (including aryl chlorides). This general and highly chemoselective protocol delivers a broad range of arylethylamine products with complete regiocontrol. The utility of this process is highlighted by its scalability and the modular synthesis of an array of bioactive small molecules.

SUBMITTER: Boyington AJ

PROVIDER: S-EPMC6444931 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Catalytic Strategy for Regioselective Arylethylamine Synthesis.

Boyington Allyson J AJ Seath Ciaran P CP Zearfoss Avery M AM Xu Zihao Z Jui Nathan T NT

Journal of the American Chemical Society 20190221 9

A mild, modular, and practical catalytic system for the synthesis of the highly privileged phenethylamine pharmacophore is reported. Using a unique combination of organic catalysts to promote the transfer of electrons and hydrogen atoms, this system performs direct hydroarylation of vinyl amine derivatives with a wide range of aryl halides (including aryl chlorides). This general and highly chemoselective protocol delivers a broad range of arylethylamine products with complete regiocontrol. The ...[more]

PMID: 30759339

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