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Lewis Acid Activation of Fragment-Coupling Reactions of Tertiary Carbon Radicals Promoted by Visible-Light Irradiation of EDA Complexes

Spencer P. Pitre, Tyler K. Allred and Larry E. Overman*

*Department of Chemistry, University of California, Irvine, California 92697-2025, United States, Email:

S. P. Pitre, T. K. Allred, L. E. Overman, Org. Lett., 2021, 23, 1103-1106.

DOI: 10.1021/acs.orglett.1c00023

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Substoichiometric amounts of a Gd(OTf)3 mediate the addition of tertiary carbon radicals generated from N-(acyloxy)phthalimide esters to cyclic α,β-unsaturated ketones and lactones. The reaction is accomplished by irradiation with visible light in the presence of Hantzsch ester without the use of a photosensitizer.

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proposed mechanism

Key Words

cyclohexanones, photochemistry, Hantzsch ester

ID: J54-Y2021