Work

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

Year: 2022

Type: article

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.

Source: Nature Communications

DOI: 10.1038/s41467-022-30393-6

Authors: Daniel M. Flores, Michael L. Neville, Valerie A. Schmidt

Institutions: University of California San Diego, Elements Biosciences (United States)

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $5,890

Funders: National Science Foundation, American Chemical Society Petroleum Research Fund, University of California, San Diego