New Catalytic Approaches to Efficient Functionalization of C-X and C-C Bonds




Dang, Hang T.

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The area of catalytic C−C and C−X (X = I, Br, Cl, OTf, ONf) functionalization has attracted enormous interest over the last century both in terms of the types of new bonds formations and the scope of transformations. Catalytic strategies employing transition metals and photoredox systems have been applied in numerous of transformation including the late-stage functionalization of natural products, pharmaceutical derivatives and in material sciences. Recently, abundant carboxylic acids have been employed as new radical precursors via decarboxylation. Herein, new catalytic approaches to efficient functionalization of C−X and C−C bonds are described. Firstly, palladium catalyzed highly regio- and stereoselective E- and Z-dienylation of C−X with 3- sulfolenes is presented, followed by the discussion on the enantioconvergent construction of α- aryl phosphonates via nickel cross coupling between aryl iodides and α-bromophosphonates. In the second section, the achievement in an acridine-catalyzed direct decarboxylative radical conjugate addition/azidative cycloaddition/sulfinylamine addition will be included. Furthermore, recent developments in boron chemistry are highlighted, including visible light induced borylation, photoinduced carboborative ring contraction and formation of boron enolates from dicarbonyl compounds.


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Acridine photocatalysis, Borylation, Decarboxylation, enantioconvergent coupling, total synthesis, transition metal catalyzed cross coupling