Zhiting Wang, Zhipeng Zheng, Xinyu Xu
Aug 22, 2018
Citations
0
Influential Citations
46
Citations
Journal
Nature Communications
Abstract
Amines are fundamental motifs in bioactive natural products and pharmaceuticals. Using simple toluene derivatives, a one-pot aminobenzylation of aldehydes is introduced that provides rapid access to amines. Simply combining benzaldehydes, toluenes, NaN(SiMe3)2, and additive Cs(O2CCF3) (0.35 equiv.) generates a diverse array of 1,2-diarylethylamine derivatives (36 examples, 56–98% yield). Furthermore, suitably functionalized 1,2-diarylethylamines were transformed into 2-aryl-substituted indoline derivatives via Buchwald–Hartwig amination. It is proposed that the successful deprotonation of toluene by MN(SiMe3)2 is facilitated by cation–π interactions between the arene and the group(I) cation that acidify the benzylic C–Hs.Amines are common targets in synthetic chemistry as they often display biological activity. Here, the authors report a one-pot aminobenzylation of aldehydes with readily available toluenes in presence of a sodium amide derivative and a cesium salt additive generating an array of valuable 1,2-diarylethylamine compounds.