Removable Tether Strategy for C—H Functionalizations

Seminar series
Organic Colloquium
Thu, Feb 28 4:00pm
CS 76
Speaker Professor Vladimir Gevorgyan
University of Illinois at Chicago
Department of Chemistry

We have developed a set of new transition metal-catalyzed C-H functionalization methodologies employing various tether strategies. These methods feature: (a) use of silyl group as a tether between a substrate and a reagent, thus transforming intermolecular reaction into an intramolecular reaction; (b) employment of a silicon-tethered directing group, which is traceless or easily convertable into valuable functionalities; (c) use of reactive silyl-tethered hydrosilane group; and (d) introduction of new N/Si-chelation concept that allows for a remote activation of aliphatic C-H bonds.

We have also uncovered new reactivity of hybrid Pd-radical species, generated at room temperature under visible light without exogenous photosensitizers, which lead to development of novel transformations, including new types of Heck reaction, aliphatic C–H functionalization methods, as well as new cascade transformations. These methods employ removable silicon-based, and amide linkers.

The scope of these transformations will be demonstrated and the mechanisms will be discussed.