The Synthetic Use of Lewis and Bronsted Acid Catalyzed Electrophilic Deborylations

With the support of the Chemical Synthesis Program in the Division of Chemistry, Professor Jeremy A. May of the University of Houston is developing new ways to couple reagents with carbon-boron bonds to other organic fragments to rapidly access complex molecular scaffolds with control of stereochemistry. These reactions proceed to form new carbon-carbon bonds with organoborane reagents and address limitations of related synthetic methodologies that require heavy metals.

This work is directed at establishing new methods to control C-C bond formation in three-dimensional molecular structures. The methodology is targeted toward improving the chemical synthesis of molecules with medicinally relevant biological activity. Professor May is also collaborating with KIPP Sharpstown Junior High, a liberal arts-focused school in Houston, to introduce the students to experimental chemistry and other physical sciences.

This partnership provides disadvantaged and at-risk students the opportunity to bolster their scientific understanding and desire to prepare for college.

Professor May and his research team are developing new ways to activate and control nucleophilic additions of organoboranes with the goal of constructing challenging carbon-carbon bonds within architecturally complex organic frameworks. Lewis and Bronsted acid catalysts will be investigated for their ability to promote these additions into a variety of electrophilic organic fragments with stereochemical control.

The transformations to be studied include examples involving heterocyclic organoboranes and other functionalities that are often incompatible with transition metal-catalyzed carbon-carbon bond forming strategies. Electrophilic deborylation approaches are further being tested in annulation reactions and natural product synthesis. These activities are expected to synergistically provide excellent training for a diverse group of graduate and undergraduate students in synthetic chemistry.

This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.