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...
Saved in:
| Main Authors: | , , , , , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
2022
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/155163 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | 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. |
|---|