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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Ambiphilic Phosphinidene-Enabled Regioselective Ring-Opening of Epoxides
Yang Li1, Zhenhai Shan1, Rongqiang Tian1
1College of Chemistry, International Phosphorus Laboratory, Zhengzhou University, Zhengzhou 450001, P. R. China.
Organic Letters
|May 14, 2026
Summary
Phosphinidene, a single atom, enables regioselective epoxide ring-opening. This novel reaction forms allyloxy phosphines and demonstrates a new strategy for small-molecule activation by low-coordinate main-group elements.
Area of Science:
- Organometallic Chemistry
- Main-Group Chemistry
Background:
- Epoxide ring-opening is a fundamental organic transformation.
- Activation of small molecules by main-group elements is an emerging field.
Purpose of the Study:
- To introduce phosphinidene as a novel reagent for epoxide ring-opening.
- To explore the regioselectivity and scope of this transformation.
- To elucidate the reaction mechanism using computational methods.
Main Methods:
- Reaction of various epoxides with phosphinidene precursors.
- Characterization of the resulting allyloxy phosphines.
- Density Functional Theory (DFT) calculations to study the mechanism.
Main Results:
- Regioselective ring-opening of epoxides was achieved using phosphinidene.
- A range of phosphinidene precursors and epoxides were compatible.
- DFT calculations supported a concerted mechanism involving simultaneous interaction with oxygen and beta-hydrogen.
Conclusions:
- Phosphinidene serves as an effective ambiphilic atom center for epoxide activation.
- This work presents a new synthetic strategy for allyloxy phosphine synthesis.
- Highlights the potential of low-coordinate main-group species in small-molecule activation.
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