One-pot aminobenzylation of aldehydes with toluenes.

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-diary- lethylamines 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-n interactions between the arene and the group(I) cation that acidify the benzylic C-Hs. [ABSTRACT FROM AUTHOR]