Bond-Forming Methods for Strained Cycloalkyl Groups in Organic and Main-Group Compounds: Applications in Catalyst Design

With the support of the Chemical Catalysis Program in the Division of Chemistry, Professor Schley at Vanderbilt University is developing new synthetic methods for the synthesis of organic molecules containing bicyclic groups. These methods will equip synthetic chemists with the means to craft molecules of increasingly complex three-dimensional shape and structure, contributing techniques to enhance innovation in the US fine chemical and specialty chemical industries. Members in Prof. Schley’s team will receive training in advanced chemistry techniques necessary to become part of a skilled and competitive workforce. Researchers at Vanderbilt University will partner with local community colleges in the greater Nashville area to establish undergraduate research and training opportunities for local Tennessee community college students to conduct research at Vanderbilt University.

With the support of the Chemical Catalysis Program in the Division of Chemistry, Professor Schley at Vanderbilt University is developing methods for the synthesis of organometallic compounds of strained bicyclic groups via radical hydrometalation of the corresponding propellanes. The resulting bicycloalkyl organometallics will be applied as nucleophilic coupling partners in palladium-catalyzed cross-coupling chemistry, and as reagents in 1,2-hydrometalation chemistry of carbonyl derivatives. Whereas existing methods primarily allow for difunctionalization of propellanes via radical reactions, the proposed methods will provide synthetic chemists with the means to introduce bicycloalkyl substituents as terminal groups through transition-metal catalyzed processes already familiar to and broadly applied in chemical industry. The conformational inflexibility of bicycloalkyl substituents accessible by this approach will be applied in the synthesis of bicycloalkyl phosphines, aiding in development of phosphine ligands for chemical catalysis.

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.

Award Number: 2453672
Principal Investigator: Nathan Schley
Funds Obligated: $380,000
State: TN