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Palladium-Catalyzed C-H Arylation of ?,?-Unsaturated Imines: Catalyst-Controlled Synthesis of Enamine and Allylic Amine Derivatives.

ABSTRACT: A unique chemo- and regioselective ?- and ?-arylation of palladium azapentadienyl intermediates is presented. Two distinct catalysts and sets of conditions successfully controlled the regioselectivity of the arylation. These methods provide the first umpolung C-H functionalization of azapentadienyl palladium intermediates and enable the divergent synthesis of allylic amine and enamine derivatives, which are of significant interest in the pharmaceutical industry.

SUBMITTER: Li M

PROVIDER: S-EPMC4887135 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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Palladium-Catalyzed C-H Arylation of α,β-Unsaturated Imines: Catalyst-Controlled Synthesis of Enamine and Allylic Amine Derivatives.

Li Minyan M González-Esguevillas María M Berritt Simon S Yang Xiaodong X Bellomo Ana A Walsh Patrick J PJ

Angewandte Chemie (International ed. in English) 20160205 8

A unique chemo- and regioselective α- and γ-arylation of palladium azapentadienyl intermediates is presented. Two distinct catalysts and sets of conditions successfully controlled the regioselectivity of the arylation. These methods provide the first umpolung C-H functionalization of azapentadienyl palladium intermediates and enable the divergent synthesis of allylic amine and enamine derivatives, which are of significant interest in the pharmaceutical industry. ...[more]

PMID: 26846375

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