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- Title
Cucurbit[7]uril‐Catalyzed Controllable Pinacol Rearrangement with Activated Hydride Migration.
- Authors
Jin, Ye; Li, Min; Liu, Mao; Ge, Qingmei; Cong, Hang; Tao, Zhu
- Abstract
A selective pinacol rearrangement of hydrobenzoin compounds was established through a heterogeneous catalysis strategy in the presence of cucurbit[7]uril. As an unexpected consequence, the ketone was generated as the sole product with the cucurbit[7]uril‐controlled hydride migration under optimized conditions. The five recycled runs suggested the catalytic activity of the cucurbit[7]uril remained. The experimental analysis and DFT calculation disclosed the important role of supramolecular encapsulation of substrates within the cavity of the macrocyclic host to fix the phenyl groups on hydrobenzoin compounds and trigger the hydride migration, therefore, ketone was the prior product.
- Subjects
PINACOL rearrangement; HYDRIDES; HETEROGENEOUS catalysis; CUCURBITACEAE; PHENYL group; CATALYTIC activity; MACROCYCLIC compounds
- Publication
European Journal of Organic Chemistry, 2022, Vol 2022, Issue 5, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202101446