Cleavage and reassembly C≡C bonds of ynones to access highly functionalized ketones
An economical strategy has been designed to formally cleave CC bonds of ynones through copper-catalyzed carbene chemistry. It proceeds under mild reaction conditions in a step-economy process by simultaneously cleaving the CC bonds and constructing C-C bonds. Depending on the substitution of the yno...
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| Main Authors: | , , , , , |
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| 其他作者: | |
| 格式: | Article |
| 語言: | English |
| 出版: |
2022
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| 主題: | |
| 在線閱讀: | https://hdl.handle.net/10356/155163 |
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| 總結: | An economical strategy has been designed to formally cleave CC bonds of ynones through copper-catalyzed carbene chemistry. It proceeds under mild reaction conditions in a step-economy process by simultaneously cleaving the CC bonds and constructing C-C bonds. Depending on the substitution of the ynones, the reactions can proceed efficiently to generate synthetically useful 1,4-ketoaldehydes and cyclopentenone compounds. A plausible pathway is proposed that involves an active cyclopropane intermediate that consequently undergoes a cascade ring-opening reaction. The method works for a spectrum of ynones and N-tosylhydrazones that give good to excellent yields using a cheap copper catalytic system. |
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