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Issue 6, 2014
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Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions

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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.

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

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The article was received on 24 Dec 2013, accepted on 26 Mar 2014 and first published on 26 Mar 2014


Article type: Edge Article
DOI: 10.1039/C3SC53526F
Citation: Chem. Sci., 2014,5, 2383-2391
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    Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions

    M. Li, B. Yücel, J. Adrio, A. Bellomo and P. J. Walsh, Chem. Sci., 2014, 5, 2383
    DOI: 10.1039/C3SC53526F

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