Synthetic Organic and Organometallic Chemistry, Catalysis
A.B. Chemistry, Harvard University (2001); Ph.D. Princeton University (2006); NIH Postdoctoral Fellow, University of Illinois at Urbana-Champaign (2006-2008)
Research in our group will focus on the general areas of reaction development and chemical synthesis. Our studies will ultimately be driven by the discovery of new and useful forms of chemical reactivity. Harnessing these new forms of chemical reactivity for the development of powerful reactions and strategies for synthesis will be a major focus. A theme of these studies will be an emphasis on catalytic transformations employing easily accessed substrates and common molecular functionality. We will also perform detailed investigations probing reaction mechanism and kinetics that is critical to understanding these processes. Complex synthesis will also be a focus of our group, as the remarkable array of unique architectures that nature provides can inspire us to develop creative solutions to challenging problems in synthesis. Brief summaries of three research directions illustrating these objectives are shown below:
Bioinspired Catalytic Alkane C-H Bond Functionalizations for Organic Synthesis:
The selective functionalization of the unactivated alkane C-H bond represents a problem in synthetic chemistry of paramount importance. The development of useful methods for alkane activation has important implications in synthetic chemistry, facilitating new modes of strategic bond construction and widening the spectrum of petrochemical-based organic feedstocks for synthetic use. This research project involves adaptations of nature's remarkable iron-dependent metalloenzymes for use in organic synthesis, to facilitate the selective oxidation and halogenation of alkanes. Our goal will be the use of easily accessed substrates, inexpensive metal sources, and oxygen as oxidant to maximize synthetic potential.
Development of Carbon-Carbon Bond-Forming Processes via Catalytic Activation of Alkyl Electrophiles:
Common methods for the activation of alkyl halides and related electrophiles for synthetic chemistry largely involve highly reactive intermediates. Transition metal catalysis could provide an attractive solution to this problem, however many transition metals only react slowly with alkyl electrophiles, and dehydrohalogenation can be problematic. This project involves the development of new approaches for the catalytic activation of alkyl electrophiles for use in synthesis employing transition metal catalysis.
New Cycloaddition Strategies for Heterocycle Synthesis:
The [2+2+2] cycloaddition reaction is a powerful tool for the construction of six-membered carbo- and heterocyclic rings. However, the majority of these reactions involve multiple alkynes or highly reactive π-components. New cycloadditions involving simple alkenes or hetero-π systems open opportunities for the rapid generation of molecular complexity from common starting materials. This project will involve the development of new approaches to six-membered ring heterocycles via the [2+2+2] cycloaddition of simple unsaturated π-systems, and will explore applications to the synthesis of a number of complex natural products.