Construction of Cyclobutanes by Multicomponent Cascade Reactions in Homogeneous Solution through Visible‐Light Catalysis
Abstract[2+2] Photocycloaddition of two olefins is a general method to assemble the core scaffold, cyclobutane, found in numerous bioactive molecules. A new approach to synthesize cyclobutanes through multicomponent cascade reactions by merging aldol reaction and Witting reaction with visible‐light‐induced [2+2] cycloaddition is reported. An array of cyclobutanes with high selectivity has been achieved from commercially available aldehydes, ketones (or phosphorus ylide), and olefins with visible‐light irradiation of a catalytic amount of ( fac‐tris(2‐phenylpyridinato‐C2,N)iridium) ([Ir(ppy)3]) at room temperature. Control experiments and spectroscopic studies revealed that the triplet–triplet energy transfer from the excited [Ir(ppy)3]* to enones, generated in situ from aldehyde and ketone or aldehyde and phosphorus ylide, is responsible for these simple and efficient muticomponent transformations..
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2019 |
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| Erschienen: |
2019 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:25 |
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| Enthalten in: |
Chemistry – A European Journal - 25(2019), 3, Seite 879-884 |
| Beteiligte Personen: |
Lei, Tao [VerfasserIn] |
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| BKL: |
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| Anmerkungen: |
© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Umfang: |
6 |
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| doi: |
10.1002/chem.201804946 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a Abstract[2+2] Photocycloaddition of two olefins is a general method to assemble the core scaffold, cyclobutane, found in numerous bioactive molecules. A new approach to synthesize cyclobutanes through multicomponent cascade reactions by merging aldol reaction and Witting reaction with visible‐light‐induced [2+2] cycloaddition is reported. An array of cyclobutanes with high selectivity has been achieved from commercially available aldehydes, ketones (or phosphorus ylide), and olefins with visible‐light irradiation of a catalytic amount of ( fac‐tris(2‐phenylpyridinato‐C2,N)iridium) ([Ir(ppy)3]) at room temperature. Control experiments and spectroscopic studies revealed that the triplet–triplet energy transfer from the excited [Ir(ppy)3]* to enones, generated in situ from aldehyde and ketone or aldehyde and phosphorus ylide, is responsible for these simple and efficient muticomponent transformations. | ||
| 700 | 1 | |a Zhou, Chao |4 aut | |
| 700 | 1 | |a Wei, Xiang‐Zhu |4 aut | |
| 700 | 1 | |a Yang, Bing |4 aut | |
| 700 | 1 | |a Chen, Bin |4 aut | |
| 700 | 1 | |a Tung, Chen‐Ho |4 aut | |
| 700 | 1 | |a Wu, Li‐Zhu |4 aut | |
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