Sulfonylation Of N-propargylamines And Diarylation Of Olefins Directed By N,S-bidentate Groups

Sulfonyl compounds and γ,γ-diaryl compounds have attracted great attention for many workers,because they are important structural units of natural products and many drugs.Among them,3-sulfonylquinoline compounds possess extensively biological activities.γ,γ-diaryl compounds are important structural elements in organic synthesis and can be further converted into other useful compounds.Therefore,this paper will focus on the sulfonation of N-propargylamines and the γ,γ-diarylation of olefins directed by N,S-bidentate groups.This paper is mainly divided into three parts:(1)The research progress of sulfonation of N-propargylamines and the difunctionalizaion of olefins is discussed;(2)A convenient and effective protocol for the synthesis of 3-sulfonated quinolines via copper-catalyzed electrophilic cyclization of N-propargylamines has been developed,in which cheap and stable sodium sulfinates were utilized as green sulfonylative reagents.This cascade transformation involves radical addition,cyclization and dehydrogenative aromatization processes in a one-pot reaction under mild conditions.(3)Assissted by N,S-bidentate directing groups,a Pd-catalyzed γ,γ-diarylation of unactivated olefins with electron-rich indoles or arylamines was developed,which provided a series of biologically important γ,γ-indole or γ,γ-diamine carbonyl compounds.The γ,γ-diarylative products can be further converted into carboxylic acids by removing the directing groups.