Cucurbit[7]uril-Catalyzed Beckmann Rearrangement of Arylketoximes

Dechao Liu; Ying Fan; Mao Liu; Qingmei Ge; Ruihan Gao; Hang Cong

doi:10.1021/acs.orglett.4c01061

Cucurbit[7]uril-Catalyzed Beckmann Rearrangement of Arylketoximes

Org Lett. 2024 Apr 26. doi: 10.1021/acs.orglett.4c01061. Online ahead of print.

Authors

Dechao Liu¹, Ying Fan^{1

2}, Mao Liu^{1

2

3}, Qingmei Ge^{1

2

3}, Ruihan Gao^{1

2}, Hang Cong^{1

2

3}

Affiliations

¹ Enterprise Technology Center of Guizhou Province, Guizhou University, Guiyang 550025, People's Republic of China.
² Collaborative Innovation Center of Guizhou Province for Efficient Utilization of Phosphorus and Fluorine Resources, Guizhou University, Guiyang 550025, People's Republic of China.
³ Engineering Research Center for Energy Conversion and Storage Technology of Guizhou, School of Chemistry and Chemical Engineering, Guizhou University, Guiyang 550025, People's Republic of China.

PMID: 38666729
DOI: 10.1021/acs.orglett.4c01061

Abstract

With the existence of cucurbit[7]uril (Q[7]), a supramolecular catalysis strategy for the Beckmann rearrangement of aryl ketoximes to N-substituted amides was successfully established. The cavity of Q[7] was found to be essential for substrate encapsulation and the rearrangement reaction through comparative experiments and studies on host-guest interactions. This supramolecular strategy provides an efficient route for the rearrangement reaction incorporating a carbonation intermediate.