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- Title
Cycloisomerization of Alkyne‐Tethered N‐Acyloxycarbamates to 2‐(3H)Oxazolones through Nitrenoid‐Mediated Carboxyamidation.
- Authors
Su, Siyuan; Wu, Tongtong; Xia, Yuanzhi; Wink, Donald J.; Lee, Daesung
- Abstract
The cycloisomerization of alkyne‐tethered N‐benzoyloxycarbamates to 2‐(3H)oxazolones is described. Two catalytic systems are tailored for intramolecular 5‐exo‐alkyne carboxyamidation and concomitant alkene isomerization. PtCl2/CO (5 mol%, toluene, 100 °C) promotes both carboxyamidation and alkene isomerization but has a limited substrate scope. On the other hand, FeCl3 (5 mol%, CH3CN, 100 °C) promotes carboxyamidation effectively but a cocatalyst is required for the exocyclic alkene isomerization. Thus, a two‐step one‐pot protocol has been developed for a broader reaction scope, which involves FeCl3‐catalyzed carboxyamidation and base‐induced alkene isomerization. Crossover experiments suggest that these reactions proceed mainly through a mechanism involving acylnitrenoid intermediates rather than carbenoid intermediates.
- Subjects
CYCLOISOMERIZATION; ALKENES; ISOMERIZATION; AMIDATION; IRON chlorides; TOLUENE
- Publication
Chemistry - A European Journal, 2023, Vol 29, Issue 19, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202203371