Specificity Orchestration in Alkynylation and Vinylation of C-H Bonds by Acetylenic and Olefinic Triflones

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The focus of this research is to achieve direct alkynylation and olefination of secondary and tertiary C-H bonds via the use of alkynyl and vinyl triflones. The research will attempt to define the mechanism of the reaction, to develop enthalpy-matched reagents for regiospecific alkynylation of complex substrates, to define appropriate protecting groups to enable selective alkynylation of unactivated tertiary C-H bonds in the presence of typically more reactive functional groups, to examine the reactions of functionalized alkynyl triflones, to use optically active acetals for the enantiospecific synthesis of acetylenic 1,3- and 1,2-diols, to seek seek alternate reagents for low temperature initiation of the alkynylation reaction, to use the reaction to induce radical cyclizations and fragmentations and to broaden the scope of the reaction to include radical-mediated olefination, dienylation, allenylation and allylation. With this award, the Synthetic Organic Program is supporting the research of Dr. Philip L. Fuchs of the Department of Chemistry at Purdue University. Professor Fuchs will focus his work on developing methodology by which to transform C-H bonds into C-C bonds. Such methodology, relying on reagents known as triflones, would provide synthetic chemists with a powerful tool with which to modify organic molecules.