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Catalytic Olefin Hydroamidation Enabled by Proton-Coupled Electron Transfer

David C. Miller, Gilbert J. Choi, Hudson S. Orbe and Robert R. Knowles*

*Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States, Email: rknowlesprinceton.edu

D. C. Miller, G. J. Choi, H. S. Orbe, R. R. Knowles, J. Am. Chem. Soc., 2015, 137, 13492-13495.

DOI: 10.1021/jacs.5b09671 (free Supporting Information)



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Abstract

Concerted proton-coupled electron transfer (PCET) mediated by an excited state iridium complex enables amide activation in the presence of a weak phosphate base to furnish a reactive amidyl radical that readily adds to pendant alkenes. The thiophenol cocatalyst furnishes the product and regenerate the active forms of the photocatalyst.

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Key Words

y-lactams, oxazolidinones


ID: J48-Y2015