Prof. Matthias Brewer (University of Vermont) Chemistry Seminar

For the past several years we have studied the reactivity of β-hydoxy-α-diazocarbonyl compounds as vinyl diazonium ion precursors. Our early work focused on taking advantage of these intermediates in-ring fragmentation reactions, which provided access to tethered aldehyde ynones and ynoates. More recently, we have been exploiting these intermediates as vinyl cation progenitors for bond-forming reactions. For example, vinyl cations act as carbene surrogates for C-H insertion reactions that give cyclopentenone products. This reactivity represents an alternative strategy to take advantage of the diazo functional group in a transition metal-free C-H insertion reaction that can provide products not accessible by the transition metal-catalyzed procedures. We have recently discovered that vinyl diazonium ions are competent electrophiles for conjugate addition reactions leading to scaffolds containing all-carbon quaternary centers while retaining the diazo group for further manipulation.  

In this presentation, I will give an overview of our vinyl cation and vinyl diazoniumion research that highlights the varied reactivity displayed by these species. Computational results that describe mechanistic features of the reactions will also be discussed.

Bio: Matthias Brewer received his Bachelor of Arts in Chemistry from the University of Vermont in 1996. His love for organic chemistry began at UVM while conducting undergraduate research with Prof. A. Paul Krapcho on the synthesis and evaluation of anti-cancer agents. After graduation, Brewer worked for one year at a biotechnology company (Leukosite), before enrolling in graduate studies in Chemistry at the University of Wisconsin-Madison, where he worked with Prof. Daniel H. Rich. Upon receiving his Ph.D. in Organic Chemistry in 2002, he joined Prof. Larry E. Overman’s research group at the University of California-Irvine as an NIH postdoctoral fellow. Brewer returned to UVM as an Assistant Professor in 2005. He was promoted to Associate Professor in 2011, and then Full Professor in2016. His research focuses on developing new synthetic organic methods and applying those methods to the synthesis of useful molecules. 

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