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Chemistry & Biochemistry Colloquium – Md Shahnawaz Ali – Hossain Research Group – Metal-Catalyzed Carbon−Carbon Bond Activation

March 31, 2017 @ 3:00 pm - 4:00 pm

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.

 

References:

1. Peng-hao Chen, Brent A. Billett, Tatsuhiro Tsukamoto, and Guangbin Dong*(2017) ‘Cut and Sew’ Transformation via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation. ACS Catal,,7,1340-1360

2. Gabriele Fumagallui, Steven Stanton, and John F. Bower*(2016), Recent Methodology that Exploit C-C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes, Chem. Reviews Article ASAP, DOI: 10.1021.acs.chemreview.6b00599

3. Boris Rybtchinski and David Milstein*(1999), Metal Insertion into C-C Bonds in Solution, Angew. Chem.Int.Ed.38,870-883

4. Ying Xia, Gang Lu, Peng Liu & Guangbin Dong* (2016) Catalytic activation of carbon-carbon in cyclopentanones. Nature, 539,546-550

Details

Date:
March 31, 2017
Time:
3:00 pm - 4:00 pm

Venue

Chemistry Room 190
3210 N. Cramer Street
Milwaukee, 53211

Organizer

Kevin Blackburn
Phone
414-229-3880