Transition-Metal-Catalyzed Reactions Via C-H Activation And Domino Reactions For Diarylation Of Propenol

Transition-metal-catalyzed C-H activation has been extensively used for the direct functionalization of organic compounds in the past few decades. However, direct and selective aliphatic C-H bonds functionalization are important and challenging tasks because aliphatic C-H bonds are ubiquitous in organic molecules and are among the least reactive bonds.As a new generation of C-C bond formations reactions, dehydrogenative cross-coupling reactions avoids prefunctionalization of both substrates, and is considered to be more efficient, atom economic and environmentally friendly. On the other hand, domino reactions have attracted great attention because they need not isolate intermediates, change reaction conditions, and add reagents or catalysts during the reaction. In this dissertation, new reactions of carbon-carbon bond formation by copper-catalyzed sp3 C-H bonds activation and palladium-catalyzed domino reactions for selective 3,3-and 1,3-diarylation of propenol are presented.1. A copper-catalyzed cascade alkylarylation reaction of 2-isocyanobiphenyls with simple alkanes for 6-alkyl phenanthridines has been developed through dual C(sp3)-H/C(sp2)-H fuctionalizations. The synthetic method has the advantages of high yields, good compatibility of functional groups and mild reaction conditions although very unreactive alkanes were involved in the reaction.2. A novel dehydrogenative cross-coupling reaction between methylquinoline derivatives and N-aryl glycine esters was developed by a cooperative catalysis of copper salt and Br(?)nsted acid, affording an efficient synthesis of β-quinolinyl a-amino acid esters.3. A new domino Heck/Saegusa/Heck reaction of propenol with aryl iodides has been developed for the synthesis of 3,3-diaryl propenals by triple transition-metal catalysis. We also developed the domino Heck-isomerization/Heck-type reaction of propenol with aryl iodides for the synthesis of 1,3-diaryl propanones by double transition-metal catalysis and the mediation of secondary amine.