Intermolecular 2+2 imine-olefin photocycloadditions enabled by Cu(I)-alkene MLCT.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 35589714.
- Also identified by DOI 10.1038/s41467-022-30393-6 and PMC identifier 9120151.
- Licence recorded as CC BY.
- The licence permits redistribution, so the abstract is shown in full and the full text is available from the publisher.
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.
Medical subject headings
- Alkenes
- Azetidines