Metal-Catalyzed Carbon−Carbon Bond Activation
By: Md Shahnawaz Ali
Department of Chemistry and Biochemistry, University of Wisconsin, Milwaukee
3210 North Cramer Street, Milwaukee, WI 53211
Advisor: Dr. M.M. Hossain
Abstract
Organic natural products, petroleum oils and polymers on earth are comprised of many C-C bonds. The advancement, especially within the last 3 decades, of potent catalytic methods for the cleavage of C-C bonds is an essential challenge in organic synthesis. The activation of C-C bond offers a way to break these extremely inert bonds to form more active linkages (e.g. between carbon & transition metal catalysts). C-C bond activation is perplexing because of the kinetic inertness of the C-C bond and the newly formed C-M bond is relatively weak. By taking advantage of the strain relief energy of 3/4 membered carbon ring opening, and by introducing a directing group/chelating group into the less/unstrained carbon ring, C-C bond cleavage is possible. A considerable number of enantioselective and regioselective studies have already been done. Natural products such as (±)-α-Agarofuran (an antitumor agent), Erogorgiaene (an active mycobacterium tuberculosis compound), Gracilamine (an antitumor & antiviral medication), Galanthamine (used for early treatment of Alzheimer diseases), as well as many other possible biologically active targets can be synthesized using regioselective C-C activation.
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