What question did this study set out to answer?

This research aims to investigate how noncovalent interactions influence regioselectivity in organocatalytic reactions.

May 10, 2026Organic Letters1 citations

Theoretical Study and Rational Design of Noncovalent Interactions Enable Organocatalytic Divergent 2+2 and 4+2 Annulations

XWXinghua WangZhengzhou University SMSiyan MiaoJiangsu Normal University YLYu LanChongqing University

Key Points

This research aims to investigate how noncovalent interactions influence regioselectivity in organocatalytic reactions.
Theoretical studies were conducted to analyze noncovalent interactions in N-heterocyclic carbene (NHC) and isothiourea catalysis.
The NHC structure was redesigned based on computational insights to alter its interaction profile.
Experimental validation was performed to confirm theoretical predictions regarding regioselectivity.
Computed noncovalent interactions successfully predicted changes in regioselectivity based on NHC structure modifications.
Experimental results aligned with theoretical predictions, demonstrating significant modulation of regioselectivity.
The study highlights the essential role of noncovalent interactions in directing reaction pathways for [2+2] and [4+2] annulations.

Abstract

Organocatalytic regiodivergent annulations represent a challenging yet powerful strategy for the rapid construction of structurally distinct products. Herein, we employ theoretical studies to reveal how noncovalent interactions govern divergent 2+2 and 4+2 annulation pathways catalyzed by N-heterocyclic carbene (NHC) and isothiourea. Guided by computational insights, the NHC structure was strategically redesigned to modulate its noncovalent interaction profile, thereby switching its original regioselectivity. Experimental validation confirmed the predictions, underscoring the pivotal role of noncovalent interactions in controlling the regioselectivity.

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