Macrocyclic 1,4-Diketones: Versatile Intermediates for the Chemical Synthesis of Complex, Congested and Constrained Molecules

Friday, March 3, 2017


Dr. Bradley Merner

Department of Chemistry and Biochemistry

Auburn University

Dr. Bradley Merner

Our group has recently demonstrated that macrocyclic 1,4-dketones can be converted into highly strained arene-bridged systems, which represent (macrocyclic) benzenoid segments of armchair carbon nanotubes (CNTs).  This non-cross-coupling-based approach enables the incorporation of strategically placed (aryl) halides that can later be engaged in programmed carbon-carbon bond forming reactions, resulting in longitudinal pi-extension of benzenoid CNT segments to polycyclic aromatic hydrocarbon (PAH) segments.  The success of this approach is due to a diastereoselective Grignard reaction, which is, in turn, dependent on the size of the macrocyclic system(s) employed.  Recent work that takes advantage of this size-dependent diastereoselectivity and its application to the synthesis of functionalized bent arene units, highly strained benzenoid macrocycles, and polyfunctionalized cyclobutanes will be discussed.

 

Bradley L. Merner was born in St. John’s, NL, Canada in 1982.  After completing his Ph.D. in 2010 under the direction of Prof. Graham Bodwell at Memorial University, he moved to the Université de Montréal to pursue postdoctoral studies with Prof. Stephen Hanessian.  While in Montréal he co-authored an advanced level organic chemistry textbook with Prof. Hanessian and Dr. Simon Giroux. In 2013, he moved to Auburn, AL to start his independent research career as an Assistant Professor in the Department of Chemistry and Biochemistry at Auburn University. In July of 2016 he was awarded the Land Professorship in Chemistry and Biochemistry.  In his spare time, he enjoys spending time with his wife Nancy, daughters Abby and Sophie, their two dogs Casey and Paddy, watching football, and coaching his daughters' soccer teams.


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