Synthesis Of Benzimidazole And Indole Derivatives VIA Copper-Catalyzed Domino Reactions

The dissertation focused on synthesis of benzimidazo[2,1-b]benzothiazole derivatives and 1,2-disubstituted indole derivatives via copper-catalyzed domino reactions.There are four chapters in this dissertation.Chapter 1 briefly reviews the study of copper-catalyzed coupling reactions and its application for the synthesis of heterocycles.Chapter 2 studies the Cu(I)-catalyzed domino coupling of o-dihaloarenes with 2-mercaptobenzimidazoles. And a variety of benzimidazo[2,1-b]benzothiazoles were synthesized. The reaction is applicable to a series of multi-functional substrates. Furthermore, scale-up experiment and Suzuki reaction of the brominated products were also achieved.Chapter 3 describes the assembly of 1,2-disubstituted indole derivatives through a Cu(II)-catalyzed domino coupling/cyclization process. Under aerobic conditions, a wide range of 1,2-disubstituted indole derivatives were efficiently and facilely synthesized from 2-alkynylanilines and boronicacids. Indolo[1,2-f]phenanthridines were obtained via Pd(II)-catalyzed intramolecular direct C(sp2)-H arylation. One-pot tandem approaches to indolo[1,2-f]phenanthridines were also achieved.Chapter 4 describes an approach to 1,2-disubstituted indole derivatives using a ligand-free copper(I)-catalyzed domino coupling/cyclization reaction of 2-alkynylanilines with aryl halides. A variety of 1,2-disubstituted indoles were generated in one pot with good to excellent yields. Furthermore, a series of indolo[1,2-f]phenanthridines were successfully assembled from the tandem reactions of 2-alkynylanilines with o-dihaloarenes through Cu(I)-catalyzed coupling/cyclization followed by Pd(II)-catalyzed intramolecular direct C(sp2)-H arylation.