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One-pot aminobenzylation of aldehydes with toluenes.

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-? interactions between the arene and the group(I) cation that acidify the benzylic C-Hs.

SUBMITTER: Wang Z

PROVIDER: S-EPMC6105668 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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One-pot aminobenzylation of aldehydes with toluenes.

Wang Zhiting Z Zheng Zhipeng Z Xu Xinyu X Mao Jianyou J Walsh Patrick J PJ

Nature communications 20180822 1

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 t ...[more]

PMID: 30135427

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