VanGelder Kelsey F, Kozlowski Marisa C
Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.
Org Lett. 2015 Dec 4;17(23):5748-51. doi: 10.1021/acs.orglett.5b02793. Epub 2015 Nov 20.
Catalytic conditions for the α-arylation of aryl nitromethanes have been discovered using parallel microscale experimentation, despite two prior reports of the lack of reactivity of these aryl nitromethane precursors. The method efficiently provides a variety of substituted, isolable diaryl nitromethanes. In addition, it is possible to sequentially append two different aryl groups to nitromethane. Mild oxidation conditions were identified to afford the corresponding benzophenones via the Nef reaction, and reduction conditions were optimized to afford several diaryl methylamines.
尽管之前有两篇报道称这些芳基硝基甲烷前体缺乏反应活性,但通过平行微量实验发现了芳基硝基甲烷α-芳基化的催化条件。该方法有效地提供了各种取代的、可分离的二芳基硝基甲烷。此外,有可能将两个不同的芳基依次连接到硝基甲烷上。确定了温和的氧化条件,通过涅夫反应得到相应的二苯甲酮,并优化了还原条件以得到几种二芳基甲胺。