In the last few decades, palladium-catalyzed cross-coupling chemistry evolved from interesting lab-scale experiments to an essential part of industrial synthetic chemistry. Numerous large scale syntheses have been developed over the years, typically for C-C, C-O and C-N bond forming reactions in medicinal chemistry. However, development of new cross-coupling reactions for the efficient transformation of less reactive but cheaper and more widely available aryl chlorides is still a challenging field organic chemistry. Our research focusses to the design and development of new reagents, catalyst and ligands for the efficient transformation of aryl chlorides to construct new carbon-carbon and carbon-heteroatom bonds. In our recent studies we developed novel C-O bond forming reactions between aryl chlorides and new type tetraalkoxy borates in efficient palladium catalyzed processes. The scope and limitation of methoxylation, trifluoroethoxylation and chloroethoxylation reactions were studied. Additionally, the applicability of the borate salts in the synthesis of some derivatives of active pharmaceutical ingredients (sildenafil, bazedoxifene, raloxifene) were demonstrated. Besides the design of novel alkoxylating agents, new formulated Pd(0) catalysts (Pd(PPh3)4 and Pd(tBu3P)2) were developed for cross-coupling reactions. The paraffinated catalysts enables the ease of use of relatively sensitive palladium complexes. Their applicability was successfully demonstrated in palladium catalyzed Sonogashira reaction of aryl-chlorides and terminal alkynes.

Development of palladium-catalyzed cross-coupling reactions for carbon-carbon and carbon-heteroatom bond forming reactions of aryl chlorides

2019 Spring National Meeting

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