Organic Chemistry Portal

Abstracts

Search:

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 (free Supporting Information)



see article for more reactions

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.

see article for more examples



Key Words

benzylamines, alkylation, multicomponent reactions


ID: J54-Y2019