化学
催化作用
钯
烯烃
反应性(心理学)
药物化学
戒指(化学)
三氟甲磺酸
烯丙基重排
环氧乙烷
有机化学
芳基
组合化学
替代医学
烷基
病理
医学
作者
Tomohiko Fujii,Qian Wang,Jieping Zhu
标识
DOI:10.1002/anie.202403484
摘要
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.
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