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Arylative Ring Expansion of 3‐Vinylazetidin‐3‐Ols and 3‐Vinyloxetan‐3‐Ols to Dihydrofurans by Dual Palladium and Acid Catalysis.
- Source :
-
Angewandte Chemie International Edition . 5/27/2024, Vol. 63 Issue 22, p1-6. 6p. - Publication Year :
- 2024
-
Abstract
- In contrast to the well‐studied 1‐vinylcyclobutanols, the reactivity of 3‐vinylazetidin‐3‐ols 1 and 3‐vinyloxetan‐3‐ols 2 under transition metal catalysis remains largely unexplored. We report herein their unique reactivity under dual palladium and acid catalysis. In the presence of a catalytic amount of Pd(OAc)2(PPh3)2, AgTFA and triflic acid, the reaction of 1 or 2 with aryl iodides affords 2,3,4‐trisubstituted dihydrofurans, which are valuable heterocycles in organic synthesis. Mechanistic studies reveal that this arylative ring‐expansion reaction proceeds via a domino process involving Heck arylation of alkene, acid‐catalyzed transposition of allylic alcohol and ring opening of the azetidine/oxetane by an internal hydroxyl group. [ABSTRACT FROM AUTHOR]
- Subjects :
- *DIHYDROFURANS
*ALLYL alcohol
*PALLADIUM
*CATALYSIS
*ARYL iodides
*ORGANIC synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 63
- Issue :
- 22
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 177321164
- Full Text :
- https://doi.org/10.1002/anie.202403484