One-pot aminobenzylation of aldehydes with toluenes

Zhiting Wang, Zhipeng Zheng, Xinyu Xu, Jianyou Mao () and Patrick J. Walsh ()
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Zhiting Wang: Nanjing Tech University
Zhipeng Zheng: University of Pennsylvania
Xinyu Xu: Nanjing Tech University
Jianyou Mao: Nanjing Tech University
Patrick J. Walsh: Nanjing Tech University

Nature Communications, 2018, vol. 9, issue 1, 1-8

Abstract: 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.

Date: 2018
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DOI: 10.1038/s41467-018-05638-y

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