Construction of Cyclobutanes by Multicomponent Cascade Reactions in Homogeneous Solution through Visible-Light Catalysis
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim..
[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 (Weinheim an der Bergstrasse, Germany) - 25(2019), 3 vom: 14. Jan., Seite 879-884 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Lei, Tao [VerfasserIn] |
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| Links: |
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| Themen: |
[2+2] photocycloaddition |
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| Anmerkungen: |
Date Completed 29.01.2019 Date Revised 29.01.2019 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/chem.201804946 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM289505798 |
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| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. | ||
| 520 | |a [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 | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Witting reactions | |
| 650 | 4 | |a [2+2] photocycloaddition | |
| 650 | 4 | |a aldol reaction | |
| 650 | 4 | |a cyclobutane | |
| 650 | 4 | |a multicomponent cascade reactions | |
| 700 | 1 | |a Zhou, Chao |e verfasserin |4 aut | |
| 700 | 1 | |a Wei, Xiang-Zhu |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Bing |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Bin |e verfasserin |4 aut | |
| 700 | 1 | |a Tung, Chen-Ho |e verfasserin |4 aut | |
| 700 | 1 | |a Wu, Li-Zhu |e verfasserin |4 aut | |
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