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 International Edition

DOI: 10.1002/anie.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