Chemoselective Intermolecular Cross-Benzoin Reactions Via Pyridinium-Zwitterion Intermediates
Nikolaos Vagkidis, Stephen M Goodlett, Peter R Schreiner · 2026
Read Chemoselective Intermolecular Cross-Benzoin Reactions Via Pyridinium-Zwitterion Intermediates by Nikolaos Vagkidis, Stephen M Goodlett, Peter R Schreiner (2026) in the Tower of Babel, a free online library of public-domain works preserved in clean, searchable text. No sign-up. The full text is served as a plain-text file at a predictable URL, where text is present: https://antarctic-labs.com/tower-of-babel/PMC13651516.txt.
Description
Nikolaos Vagkidis and two co-authors open a new route into the benzoin reaction, a polarity-reversing coupling known since 1832, by taming hydroxycarbenes. These fleeting intermediates normally snap into aldehydes almost at once through quantum tunneling, which kept them out of practical synthesis.
The team extended a pyridine probe method to catch the carbenes the moment they formed, freezing them as lasting zwitterionic intermediates, charged but overall neutral species. Those trapped intermediates then reacted with many aldehydes to give cross-benzoin products in high yields, strongly favoring the desired pairing. Mass spectrometry gave the first full picture of such intermediates, and calculations backed how they form and react. The authors present nucleophilic trapping as a general tool for putting hydroxycarbene reactivity to work rather than watching it vanish.
Catalog record
| CREATOR | Nikolaos Vagkidis, Stephen M Goodlett, Peter R Schreiner |
|---|---|
| YEAR | 2026 |
| COLLECTION | PAPERS |
| FORMAT | TXT |
| FILE SIZE | 32 KB |
| LICENSE | This article is licensed under CC-BY 4.0 |
| RIGHTS | CC BY |
| SOURCE | Europe PMC |