期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 22, 页码 8741-8745出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b03775
关键词
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资金
- University of California, San Diego
- USDoEd GAANN Fellowship [P200A150251-17]
Photocycloadditions are often typified by the oxetane-forming Paterno-Buchi 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) precatalyst 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.
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