Synthesis of diarylmethylaminesviapalladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.
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 ofin situgenerated 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.
Department of Chemistry, University of Pennsylvania, 231 S. 34th St., Philadelphia, PA 19104, USA. Web: http://titanium.chem.upenn.edu/walsh/index.html.
Minyan
M
Li
Department of Chemistry, University of Pennsylvania, 231 S. 34th St., Philadelphia, PA 19104, USA. Web: http://titanium.chem.upenn.edu/walsh/index.html ; Istanbul Technical University, Department of Chemistry, 34469 Maslak, Istanbul, Turkey.
Baris
B
Yücel
Department of Chemistry, University of Pennsylvania, 231 S. 34th St., Philadelphia, PA 19104, USA. Web: http://titanium.chem.upenn.edu/walsh/index.html ; Universidad Autónoma de Madrid, Facultad de Ciencias, Departamento de Química Organica, Cantoblanco, 28049 Madrid, Spain.
Javier
J
Adrio
Department of Chemistry, University of Pennsylvania, 231 S. 34th St., Philadelphia, PA 19104, USA. Web: http://titanium.chem.upenn.edu/walsh/index.html.
Ana
A
Bellomo
Department of Chemistry, University of Pennsylvania, 231 S. 34th St., Philadelphia, PA 19104, USA. Web: http://titanium.chem.upenn.edu/walsh/index.html.
Patrick J
PJ
Walsh