A chelating nucleophile plays a starring role: 1,8-naphthyridine-catalyzed polycomponent α,α-difluorination of acid chlorides.
| Publication Type | Academic Article |
| Authors | Griswold A, Bloom S, Lectka T |
| Journal | J Org Chem |
| Volume | 79 |
| Issue | 20 |
| Pagination | 9830-4 |
| Date Published | 09/26/2014 |
| ISSN | 1520-6904 |
| Abstract | A dually activated ketene enolate, generated from an acid chloride, the unusual chelating nucleophile (1,8-naphthyridine), and a Lewis acid, reacts to afford a host of α,α-difluorinated products in the presence of a benchtop-stable fluorinating agent (Selectfluor). The use of this method to synthesize otherwise difficult to make products is highlighted along with computational and spectroscopic support for the proposed chelate. |
| DOI | 10.1021/jo501534k |
| PubMed ID | 25222052 |