Alkaline-Metal-Catalyzed One-Pot Aminobenzylation of Aldehydes with Toluenes

Guoqing Liu, Patrick J. Walsh* and Jianyou Mao*

*Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, P.R. China; University of Pennsylvania, Pennsylvania 19104-6323, United States, Email: ias_jymaonjtech.edu.cn, pwalshsas.upenn.edu

G. Liu, P. J. Walsh, J. Mao, Org. Lett., 2019, 21, 8514-8518.

DOI: 10.1021/acs.orglett.9b02737

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Abstract

A metal bis(trimethylsilyl)amide/Cs₂CO₃ co-catalyzed benzylation of in situ generated N-(trimethylsilyl) aldimines with toluene derivatives provides a diverse array of bioactive 1,2-diarylethylamines with excellent efficiency and broad functional group tolerance. The catalyst exhibits high chemoselectivity for deprotonation of toluenes at the benzylic position.

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Key Words

benzylamines, alkylation, multicomponent reactions

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ID: J54-Y2019