In this work we target new methods to prepare the cyclobutane carbon scaffold, a structural feature found in both natural and artificial molecules. It has long been known that cyclobutane rings can be synthesized from two carbon-carbon double bonds through activation with ultraviolet (UV) light; however, UV light sources are expensive, hazardous to use, and often lead to uncontrollable reactivity. To avoid the challenges of using high-energy UV light, our reactions were carried out under lower energy visible light (blue LEDs). In this project, we report on investigation of the intermolecular [2 + 2] cycloaddition of a functionalized vinylogous ester and vinylogous amide heterocycles with simple alkene coupling partners. We base this work on previous cycloadditions accomplished in our laboratory featuring heterocycles with both an electron deficient and electron rich substitution. Results, to date, will be reported. The scope of this work will include efforts to understand the mechanism by which this cycloaddition occurs.

Visible-light promoted synthesis intramolecular [2 + 2] cycloadditions of vinylogous ester and amide heterocycles

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ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.