Intermolecular 2+2 imine-olefin photocycloadditions enabled by Cu(I)-alkene MLCT

Daniel M. Flores, Michael L. Neville and Valerie A. Schmidt ()
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Daniel M. Flores: University of California San Diego, Department of Chemistry and Biochemistry
Michael L. Neville: University of California San Diego, Department of Chemistry and Biochemistry
Valerie A. Schmidt: University of California San Diego, Department of Chemistry and Biochemistry

Nature Communications, 2022, vol. 13, issue 1, 1-6

Abstract: Abstract 2 + 2 Photocycloadditions are idealized, convergent construction approaches of 4-membered heterocyclic rings, including azetidines. However, methods of direct excitation are limited by the unfavorable photophysical properties of imines and electronically unbiased alkenes. Here, we report copper-catalyzed photocycloadditions of non-conjugated imines and alkenes to produce a variety of substituted azetidines. Design principles allow this base metal-catalyzed method to achieve 2 + 2 imine-olefin photocycloaddition via selective alkene activation through a coordination-MLCT pathway supported by combined experimental and computational mechanistic studies.

Date: 2022
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DOI: 10.1038/s41467-022-30393-6

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