二芳基甲胺的合成：钯催化1,1,3-三芳基-2-氮杂烯丙基阴离子的区域选择性芳基化反应。
Synthesis of diarylmethylamines palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.
作者信息
Li Minyan, Yücel Baris, Adrio Javier, Bellomo Ana, Walsh Patrick J
机构信息
Department of Chemistry, University of Pennsylvania, 231 S. 34th St., Philadelphia, PA 19104, USA. Web: http://titanium.chem.upenn.edu/walsh/index.html.
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.
出版信息
Chem Sci. 2014 Jun 1;5(6):2383-2391. doi: 10.1039/C3SC53526F.
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 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.
二芳基甲胺因其在药物化学中的广泛存在而备受关注。因此，需要合成它们的新方法。在此，我们报道了一种通用的合成二芳基甲胺衍生物的方法，该方法涉及钯催化由生成的2-氮杂烯丙基阴离子中间体进行的芳基化反应。2-氮杂烯丙基阴离子通过易于获得的醛亚胺和酮亚胺前体的可逆去质子化生成。重要的是，芳基化的醛亚胺和酮亚胺产物在反应条件下不会发生异构化。还成功地进行了芳基化反应的放大以及将所得产物水解以提供二芳基甲胺。
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