| Autor: |
Tryniszewski M; Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland., Basiak D; Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland., Barbasiewicz M; Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland. |
| Jazyk: |
angličtina |
| Zdroj: |
Organic letters [Org Lett] 2022 Jun 17; Vol. 24 (23), pp. 4270-4274. Date of Electronic Publication: 2022 Jun 02. |
| DOI: |
10.1021/acs.orglett.2c01604 |
| Abstrakt: |
Methanedisulfonyl fluoride, CH 2 (SO 2 F) 2 , transforms aromatic aldehydes into β-arylethenesulfonyl fluorides, useful substrates for the SuFEx "click"-type transformations. The reaction mimics mechanism of the Horner-Wadsworth-Emmons olefination, which runs via addition of the carbanion, followed by cyclization-fragmentation of the four-membered ring intermediate. In the absence of base, electron-rich aldehydes follow an alternative pathway of the Knoevenagel condensation to provide unsaturated 1,1-disulfonyl fluorides. We demonstrate also trapping of elusive ethene-1,1-disulfonyl fluoride, CH 2 ═C(SO 2 F) 2 , with 4-(dimethylamino)pyridine (DMAP) that forms zwitterionic adduct, characterized with X-ray studies. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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