Professor Thomas Hoye

CSENG Chemistry
College of Science & Engineering
Twin Cities
Project Title: 
The Hexadehydro-Diels-Alder Reaction

Most of the work in the Hoye labs involves investigations of the HDDA (hexadehydro-Diels-Alder) reaction. Their initial findings were published in the journal Nature in 2012. As they continue to discover new types of chemical transformations involving the HDDA reaction, they rely on the aid of computational chemistry to help explain results and guide them in future directions. They have recently been discovering new reactions of HDDA-generated arynes with various traps. Examples include (but are not limited to): Cu(I) mediated alkynation, BF3-promoted carbene-like C-H insertions, cascade reactions with 1,3-diynes to give polycyclic aromatic hydrocarbons (PAHs), multicomponent reactions with cyclic amines and protic nucleophiles, and reactions to synthesize natural products. The researchers have even observed that HDDA benzynes can trap furans intramolecularly! More recently, work is underway to develop "traceless tether" HDDA reactions. DFT calculations are used to probe the HDDA energetics of these new HDDA substrates, and are crucial in substrate design for this project.

In conjunction with the Center for Sustainable Polymers, these researchers are currently investigating a broad range of sustainable monomers that will engage in ROP (Ring-Opening Polymerization) processes to evaluate new polymeric materials with unique properties. Typically, these lactones and lactams are derived from natural, renewable resources, and display a variety of functionalization and substitution on the cyclic monomer core. MSI resources are used to compute the energetics of new classes of monomeric substrates via an isodesmic reaction model. The data obtained can then be assessed against experimentally determined thermodynamic and entropic values (typically with linear regression analysis), and ultimately developed into a model system that can forecast suitable reaction temperature and concentration for the polymerization of novel monomer systems.

Project Investigators

Elson Santiago de Alvarenga
Sahil Arora
Lucas Fluegel
Professor Thomas Hoye
Mengyuan Jin
Daniel Lee
Rongrong Lin
Sai Pavan Nannapaneni
Annika Page
Lindsay Robinson
Severin Thompson
Xiao Xiao
Shu Xu
Juntian Zhang
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