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Umpolung Synthesis of Diarylmethylamines via Palladium-Catalyzed Arylation of N-Benzyl Aldimines.

ABSTRACT: An umpolung synthesis of diarylmethylamine derivatives is presented. This reaction entails a Pd catalyzed arylation of 1,3-diaryl-2-azaallyl anions, in situ generated from N-benzyl aldimines. A Pd(NIXANTPHOS)-based catalyst together with hindered silylamide bases enabled the coupling of aldimines with aryl bromides in good to excellent yields without product isomerization. Moreover, regioselectivity in the arylation of unsymmetrical 1,3-diaryl-2-azaallyl anions was studied. This method is suitable for a gram scale synthesis of diarylmethylamine derivatives at room temperature without use of a glovebox.

SUBMITTER: Li M

PROVIDER: S-EPMC5298571 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

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Umpolung Synthesis of Diarylmethylamines via Palladium-Catalyzed Arylation of N-Benzyl Aldimines.

Li Minyan M Yucel Baris B Jiménez Jacqueline J Rotella Madeline M Fu Yue Y Walsh Patrick J PJ

Advanced synthesis & catalysis 20160512 12

An umpolung synthesis of diarylmethylamine derivatives is presented. This reaction entails a Pd catalyzed arylation of 1,3-diaryl-2-azaallyl anions, in situ generated from N-benzyl aldimines. A Pd(NIXANTPHOS)-based catalyst together with hindered silylamide bases enabled the coupling of aldimines with aryl bromides in good to excellent yields without product isomerization. Moreover, regioselectivity in the arylation of unsymmetrical 1,3-diaryl-2-azaallyl anions was studied. This me ...[more]

PMID: 28190996

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