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Intermolecular 2+2 Carbonyl-Olefin Photocycloadditions Enabled by Cu(I)-Norbornene MLCT.

著者 Flores DM , Schmidt VA
J Am Chem Soc.2019 May 22 ; ():.
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Photocycloadditions are often typified by the oxetane forming Paternò-Büchi reaction. However, the mechanistic constraints of carbonyl excitation and olefin interception have limited this attractive oxetane forming pathway. Here we describe the use of a Cu(I) pre-catalyst that achieves selective olefin activation via coordination to the metal center. Significantly, this intermolecular 2+2 carbonyl-olefin photocycloaddition engages alkyl ketones which are more challenging to accommodate via direct irradiation pathways. Mechanistic investigations support the in situ formation of a Cu-norbornene resting state that undergoes a MLCT leading to oxetane formation.
PMID: 31117662 [PubMed - as supplied by publisher]
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