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Abstract Ketones are among the most useful functional groups in organic synthesis, and they are commonly encountered in a broad range of compounds with various applications. Herein, we describe the mesoionic carbene‐catalyzed coupling reaction of aldehydes with non‐activated secondary and even primary alkyl halides. This metal‐free method utilizes deprotonated Breslow intermediates derived from mesoionic carbenes (MICs), which act as super electron donors and induce the single‐electron reduction of alkyl halides. This mild coupling reaction has a broad substrate scope and tolerates many functional groups, which allows to prepare a diversity of simple ketones as well as bio‐active molecules by late‐stage functionalization.
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This content will become publicly available on May 28, 2026
Switching mesoionic carbene-organocatalysis from radical to ionic pathway through base-controlled formation of Breslow intermediates versus Breslow enolates
Base-controlled formation of Breslow intermediatesversusBreslow enolates has been achieved with mesoionic carbenes. Of particular interest is the coupling of aldehydes and alkyl halides to yield ketonesviaan ionic pathway.
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- Award ID(s):
- 2153475
- PAR ID:
- 10634616
- Publisher / Repository:
- Royal Society of Chemistry
- Date Published:
- Journal Name:
- Chemical Science
- Volume:
- 16
- Issue:
- 21
- ISSN:
- 2041-6520
- Page Range / eLocation ID:
- 9163 to 9168
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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