Copper(II)-Catalyzed Three-Component Arylation/Hydroamination Cascade from Allyl Alcohol: Access to 1-Aryl-2-sulfonylamino-propanes

J Org Chem. 2023 Oct 6;88(19):13995-14003. doi: 10.1021/acs.joc.3c01536. Epub 2023 Sep 25.

Abstract

A new straightforward approach to 1-aryl-2-aminopropanes using easily accessible substrates has been developed. Simple allyl alcohol is shown to be an ideal synthetic equivalent of the C3 propane-1,2-diylium bis-cation synthon in three-component cascade reactions with arenes and sulfonamide nucleophiles to regioselectively afford 1-aryl-2-aminopropanes. The reaction is catalyzed by Cu(OTf)2 and is expected to involve a Friedel-Crafts-type allylation of the arene, followed by hydroamination.