Research at the Alabugin group

New reactions for organic synthesis, biochemistry and materials science

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Dynamic covalent chemistry: a new tool in the design of chemoselective radical reactions

We found that remarkable chemo- and regio-selectivity of the initial radical attack in multifunctional substrates can be accomplished via the combination of Dynamic Covalent Chemistry (DCC) with kinetic self-sorting. Not only is the addition of Sn-radicals to alkenes and alkynes fast and reversible but we have also identified a new 1,2 stannyl shift as a low-barrier mechanism for the conversion of an unproductive vinyl radical to the radical adduct which can undergo fast 5-exo-trig closure (serving as a route for kinetic self-sorting). Furthermore, we have also identified substitution patterns that can selectively direct the initially formed cyclic radical to react further in one of the following three ways: H-abstraction, β-scission and, ring expansion.

Selected publications:

Alkenes as Alkyne Equivalents in Radical Cascades Terminated by Fragmentations: Overcoming Stereoelectronic Restrictions on Ring Expansions For the Preparation of Expanded Polyaromatics. Mohamed, R.; Mondal, S.; Gold, B.; Evoniuk, C. J.; Banerjee, T.; Hanson, K.; Alabugin, I. V. J. Am. Chem. Soc., 2015, 137, 6335-6349. http://pubs.acs.org/doi/abs/10.1021/jacs.5b02373.

Drawing from a pool of radicals for the design of selective enyne cyclizations. Mondal, S.; Mohamed, R. K.; Manoharan, M.; Phan, H.; Alabugin, I. V. Org. Lett., 2013, 15, 5650–5653. http://pubs.acs.org/doi/abs/10.1021/ol4028072.

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Contact us:
Department of Chemistry & Biochemistry
Florida State University
Tallahassee, FL 32306-4390
E-mail: alabugin at chem.fsu.edu
Office: (850)644-5795
Fax: (850)644-8281

Our work is supported by the National Science Foundation.