期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2022, 期 5, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202101446
关键词
Cucurbit[7]uril; DFT calculation; Hydride migration; Pinacol rearrangement; Supramolecular catalysis
资金
- National Natural Science Foundation of China [22002027]
- Project of Science and Technology of Guizhou Province [[2018]5781, [2020]1Y036]
- Project of Natural Science Special Scientific Research Foundation of Guizhou University [(2019)02]
- Project of Talent Introduction of Guizhou University [(2018)47]
- Science Foundation for Postgraduated Students of Guizhou Province YJSCXJH [[2020]046]
In this study, a selective pinacol rearrangement of hydrobenzoin compounds was achieved through a heterogeneous catalysis strategy in the presence of cucurbit[7]uril. Unexpectedly, the ketone was generated as the sole product under optimized conditions due to the cucurbit[7]uril-controlled hydride migration. The catalytic activity of cucurbit[7]uril was confirmed through five recycled runs. The experimental analysis and DFT calculation revealed the crucial role of supramolecular encapsulation in fixing the phenyl groups on hydrobenzoin compounds and triggering the hydride migration, leading to the preferential formation of ketone.
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.
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