From the journal:

Chemical Communications

Controlling Lewis acid-catalysed bicyclobutane cycloadditions: carbonyl substituents dictate electrophilic vs. nucleophilic addition pathways

Dan Liu,a   Ning Wang,bc   Yuhong Yang,bc   Qing Zoub  and  Xiaoyong Zhang ORCID logo *b  

* Corresponding authors

a School of Science, Changchun Institute of Technology, Changchun 130012, China

b Guangdong Provincial Key Laboratory of Mathematical and Neural Dynamical Systems, School of Sciences, Great Bay University, Dongguan, China
E-mail: zhangxiaoyong@gbu.edu.cn

c Department of Chemistry, Southern University of Science and Technology, Shenzhen, China

Abstract

Combined DFT and DLPNO-CCSD(T) mechanistic studies reveal that carbonyl substituents of bicyclobutane (BCB) dictate the reaction pathways in Lewis acid-catalysed BCB-imine cycloadditions, toggling between electrophilic and nucleophilic additions, as well as concerted and stepwise ring-opening/addition mechanisms.

Graphical abstract: Controlling Lewis acid-catalysed bicyclobutane cycloadditions: carbonyl substituents dictate electrophilic vs. nucleophilic addition pathways

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Article information

DOI
https://doi.org/10.1039/D5CC04816H
Article type
Communication
Submitted
24 Aug 2025
Accepted
10 Nov 2025
First published
11 Nov 2025
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2025, Advance Article

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Controlling Lewis acid-catalysed bicyclobutane cycloadditions: carbonyl substituents dictate electrophilic vs. nucleophilic addition pathways

D. Liu, N. Wang, Y. Yang, Q. Zou and X. Zhang, Chem. Commun., 2025, Advance Article , DOI: 10.1039/D5CC04816H

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