Work

Photoredox‐Catalyzed Decarboxylation of Oxetane‐2‐Carboxylic Acids and Unique Mechanistic Insights

Year: 2024

Type: article

Abstract: Oxetanes are valuable motifs in medicinal chemistry applications, with demonstrated potential to serve as bioisosteres for an array of functional groups. Through the visible‐light‐mediated photoredox hydrodecarboxylation of 2‐aryl oxetane 2‐carboxylic acids this work enables access to the products of a [2+2]‐photocycloaddition between alkenes and aryl aldehydes without the challenges associated with a traditional UV‐light‐mediated Paternò‐Büchi reaction. Investigation into the hydrodecarboxylation mechanism reveals substrate‐dependent modes of initiation under the conditions reported herein. Divergence in diastereomeric outcome is observed, with mechanistic probes elucidating key hydrogen‐bonding and steric interactions.

Source: Angewandte Chemie

DOI: 10.1002/ange.202405125

Authors: Elvis C. McFee, Katie A. Rykaczewski, Corinna S. Schindler

Institution: University of Michigan

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Science Foundation, Division of Chemistry

Awards: G2391795087, NSF Center for the Chemistry of Molecularly Optimized Networks