Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover

James P. Phelan, Simon B. Lang, Jordan S. Compton, Christopher B. Kelly, Ryan Dykstra, Osvaldo Gutierrez* and Gary A. Molander*

*University of Maryland, College Park, Maryland 20742; University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States, Email: ogsumd.edu, gmolandrsas.upenn.edu

J. P. Phelan, S. B. Lang, J. S. Compton, C. B. Kelly, R. Dykstra, O. Gutierrez, G. A. Molander, J. Am. Chem. Soc., 2018, 140, 8037-8047.

DOI: 10.1021/jacs.8b05243

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Abstract

The use of the benchtop stable triethylammonium bis(catecholato)iodomethylsilicate as bifunctional reagent in combination with an organic photocatalyst and visible light enables a cyclopropanation of an array of olefins, including trifluoromethyl- and pinacolatoboryl-substituted alkenes in a matter of hours. The reaction is highly tolerant of traditionally reactive functional groups (carboxylic acids, basic heterocycles, alkyl halides, etc.).

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4CzIPN

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Radical/Polar Annulation Reactions (RPARs) Enable the Modular Construction of Cyclopropanes

J. A. Milligan, J. P. Phelan, V. C. Polites, C. B. Kelly, G. A. Molander, Org. Lett., 2018, 20, 6840-6844.

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Key Words

cyclopropanes, photochemistry

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ID: J48-Y2018