Rhodium-Catalyzed Directed C-H Bond Activation And Annulation Reactions With Alkynes

Cyclic compounds have played an indispensable role in the field of organic synthesis. In recent years, Rh(?)-catalyzed oxidative coupling of C-H bonds with alkynes has been identified as the most direct and efficient way to construct(hetero)cyclic compounds. This thesis focused on developing new methods about Rh(?)-catalyzed directed C-H activation/annulation of arenes with alkynes, and the syntheses of a variety of cyclic compounds at the same time.Organophosphines have been widely used in modern organic synthesis, especially as ligands for a variety of transition-metal-catalyzed reactions. This thesis has established a Rh(?)-catalyzed redox-neutral C-H activation/annulation reaction of N-(pivaloyloxy)benzamides with 1-alkynylphosphine sulfides, followed by desulfidation, to afford a new type of bulky phosphines with an isoquinolin-1(2H)-one motif. This method is featured by high efficiency and regioselectivity, good functional group tolerance, and mild reaction conditions, which offers a novel access for construction of new bulky phosphines.Polycyclic aromatic hydrocarbons have ubiquitous applications as ?-conjugated functional materials because of their electrochemical and photochemical properties. Indolines are basic motifs found in a variety of natural products and organic dyes. This thesis has demonstrated that 2,3-dihydro-1H-benzo[g]indolines derivatives can be constructed efficiently by Rh(?)-catalyzed oxidative annulations of N-formyl indolines with alkynes. The reaction involves the cleavage of two C-H bonds and the formation of two C-C bonds.