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

02 January 2025, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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.

Keywords

Cyclopropenation
Oxazolation
Cobalt
Metalloradical catalysis
Carbene

Supplementary materials

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Supporting Information
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Experimental details, materials, and methods, characterization data, and NMR spectra for all compounds
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