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Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

ABSTRACT: Diarylmethylamines are of great interest due to their prevalence in pharmaceutical chemistry. As a result, new methods for their synthesis are in demand. Herein, we report a versatile protocol for the synthesis of diarylmethylamine derivatives involving palladium-catalyzed arylation of in situ generated 2-azaallyl anion intermediates. The 2-azaallyl anions are generated by reversible deprotonation of readily available aldimine and ketimine precursors. Importantly, the arylated aldimine and ketimine products do not undergo isomerization under the reaction conditions. Scale-up of the arylation and hydrolysis of the resulting products to furnish diarylmethylamines were also successfully performed.

SUBMITTER: Li M

PROVIDER: S-EPMC4225812 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature

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Synthesis of diarylmethylamines <i>via</i> palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Li Minyan M Yücel Baris B Adrio Javier J Bellomo Ana A Walsh Patrick J PJ

Chemical science 20140601 6

Diarylmethylamines are of great interest due to their prevalence in pharmaceutical chemistry. As a result, new methods for their synthesis are in demand. Herein, we report a versatile protocol for the synthesis of diarylmethylamine derivatives involving palladium-catalyzed arylation of <i>in situ</i> generated 2-azaallyl anion intermediates. The 2-azaallyl anions are generated by reversible deprotonation of readily available aldimine and ketimine precursors. Importantly, the arylated aldimine an ...[more]

PMID: 25396041

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