Research

We are a newly established research group that is applying “systems” and supramolecular ways of thinking to solve problems in catalysis as it relates to organic chemistry and the chemical origins of life. Interrelated areas of focus include:

1) Aggregation in Brønsted acid catalysis

We have discovered that Brønsted acids form higher order aggregates with certain weak H-bond accepting template molecules (often solvents), which in some cases renders them dramatically more competent catalysts. We are working to deepen our understanding of this phenomenon and to exploit it to develop reactions of interest for organic synthesis, such as the direct nucleophilic substitution of alcohols [1][2] and alkyl fluorides.[3]

[1] (a) Angew. Chem. Int. Ed. 2017, 56, 3085. (b)  J. Am. Chem. Soc. 2015, 137, 9555. (c) Org. Biomol. Chem. 2014, 12, 5990. [2] For our review of catalytic dehydrative alcohol substitution, see Synthesis 2016, 48, 935. [3] (a) ACS Catalysis 2016, 6, 3670. (b)  J. Fluor. Chem. 2017, 193, 45.

2) Catalyst discovery using complex mixtures – a systems approach

toc-synpacts

We have developed a simple algorithmic approach for screening and deconvoluting complex mixtures of catalyst components with the goal of rapidly identifying new catalysts and cooperative effects.[1] We have used this strategy to uncover new organoboron [2] and nickel [2][3] catalysts, and have found that catalysts selected in this way tend to be useful in multicatalysis.[4] The continuing goal of this project is to discover new  cooperative effects and multicatalytic processes.

[1] For an account of our recent work in this area, see: Synlett 2016, 27, 2637. [2] Chem. Sci. 2015, 6, 2501. [3] J. Org. Chem. 2015, 80, 6922. [4] Chem. Eur. J. 2016, 22, 12274.

3) Self-organized reaction networks to understand the origin of life

metabolism

We are investigating the possibility that core biological anabolic pathways present in early life may have originated as non-enzymatic, possibly prebiotic, chemical pathways.  Thus far our experimental investigations have focused on two ancient CO2-fixation pathways, the acetyl CoA pathway [1] and the reverse Krebs cycle [2]. This project will illuminate how and why life’s biochemistry originated and help explain why it works the way that it does.

[1] bioRxiv 2017, doi: 10.1101/235523 (pre-print). [2] Nature Eco. Evo. 2017, 1, 1716-1721.

4) Vibrational Strong Coupling for organic chemistry and catalysis

TOC graphic

Vibrational strong coupling (VSC) allows a vibrational state to be partitioned into two energetically distinct states. A collaboration between our group and the group of Prof. Thomas Ebbesen, a world leader in VSC, aims to exploit this phenomenon for use in organic synthesis and catalysis. Thus far, we have shown that VSC can be used to change the rates of ground state organic reactions.[1] Ongoing work aims to use VSC to modulate selectivity, to understand which functional groups and reaction mechanisms are most susceptible to VSC, as well as to explore the effect of VSC on catalysis.

[1] Angew. Chem. Int. Ed. 2016, 55, 11462.

For more information on ongoing projects, please contact Dr. Moran directly.