Work

Cobaloxime‐Based Metalloradical Catalysis: A Versatile Strategy for the Synthesis of Cyclopropenes and Oxazoles

Year: 2025

Type: article

Abstract: Metalloradical catalysis (MRC), predominantly exemplified by metalloporphyrin complexes, has emerged as a promising strategy for regulating radical reactions and broadening their synthetic applications. Here, an efficient catalytic method has been devised for the radical [2 + 1] cyclopropenation of alkynes and radical [3 + 2] oxazolation of nitriles using α-aryldiazoacetates via MRC. Cobaloxime proves effective in facilitating the metalloradical [2 + 1] cyclopropenation of alkynes and radical [3 + 2] oxazolation cycloaddition reaction under mild conditions. The reactions demonstrate broad substrate tolerance, accommodating gram-scale transformations and the synthesis of pharmaceutical compounds. Our findings highlight the significant potential of cobaloxime-catalyzed cycloaddition as a valuable tool in organic synthesis and broaden the scope of metalloradical systems in catalysis.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202500667

Authors: Liming Tan, Keyang Wu, Gang Li

Institution: Utah State University

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, Utah State University, Division of Chemistry

Awards: G196131894, MRI: Acquisition of a 500 MHz NMR to Enhance Research and Training