Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 14, Pages 9257-9269Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01273
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Funding
- Ministry of Science and Technology of China [2017YFA0206903]
- National Natural Science Foundation of China [21861132004, 21473227]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB17000000]
- Key Research Program of Frontier Sciences of the Chinese Academy of Sciences [QYZDY-SSW-JSC029]
- K. C. Wong Education Foundation
- Chinese Academy of Sciences
- US National Science Foundation [CHE-1807729]
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Photosensitization has recently re-emerged owing to the current interest in visible-light catalysis. One of the photoreactions investigated in this context, namely, photo[2+2]cycloaddition of olefins, is established to show high selectivity and wide generality. Here, we describe the results of our studies on selective intermolecular cycloaddition between extended enones (2,4-dien-l-ones and 2-oxo-3-enoates) and olefins under visible-light sensitization. With Ru(bpy)(3)Cl-2 as the triplet energy sensitizer, [2+2] addition of 2,4-dien-l-ones to olefins resulted in the addition to the ene part of enones with high efficiency. Generality and functional group tolerance were established by examining a number of enones. 2-Oxo-3-enoates also underwent addition to olefins in the presence of Ru(phen)(3)(PF6)(2). Both additions were more efficient in the presence of the triplet sensitizer than upon direct irradiation. No Paterno-Buchi product was detected. Density functional theory calculations revealed the origin of high selectivity in the two extended enone systems. Together with spectroscopic studies and control experiments, the cycloaddition has been demonstrated to occur from the excited triplet state of these extended enones, which were generated via the energy transfer process.
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