Work

Regioisomeric Tuning of Intermolecular Diels‐Alder Reaction by Electrostatic Field‐Dipole Interaction

Year: 2025

Type: article

Abstract: The effect of an electric field on the regioselectivity of the Diels‐Alder reaction is explored using a zwitterionic iminium ion species as both the dienophile and the source of the electric field. The head‐to‐tail dipolar orientation of the substrates becomes favored in less‐polar solvents and at higher temperatures where the internal electric field is conserved. Computational studies validate the electric field effect on the experimental regioisomeric preferences, in terms of the transition dipole moment, reactant complexation, and transition energy. This work offers deeper insight into the effects of electrostatic fields on chemical reactions, suggesting new directions for controlling reaction selectivity.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.70044

Authors: Jinwoo Kim, Xavier Roy, Tomislav Rovis

Institutions: Chungnam National University, Columbia University

Language: English

Topic: Organic Chemistry Cycloaddition Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Science Foundation, Division of Chemistry

Awards: G3698872787, G5760180034, CCI Phase I: NSF Center for Chemistry with Electric Fields (ChEF)