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May 16, 2026Organic Letters0 citations

Ambiphilic Phosphinidene-Enabled Regioselective Ring-Opening of Epoxides

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YLYang LiZSZhenhai ShanRTRongqiang Tian

Key Points

  • This research aims to explore the role of phosphinidene in the regioselective ring-opening of epoxides.
  • Utilized various phosphinidene precursors and epoxides for the transformation.
  • Conducted DFT calculations to analyze the mechanism.
  • Investigated the formation of allyloxy phosphines through this reaction.
  • Successfully achieved regioselective ring-opening of epoxides with phosphinidene.
  • DFT calculations indicate a concerted mechanism with simultaneous interaction with oxygen and β-hydrogen.

Abstract

We disclose the use of phosphinidene as a single ambiphilic atom center that enables regioselective ring-opening of epoxides. A range of phosphinidene precursors and various epoxides are compatible with this transformation, affording the corresponding allyloxy phosphines. DFT calculations support a concerted mechanism in which the phosphinidene simultaneously interacts with both the oxygen atom and the β-hydrogen of the epoxides. This work offers a new strategy for small-molecule activation by low-coordinate main-group species.

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Cite This Study

Li et al. (2026) studied this question.

synapsesocial.com/papers/6a080acea487c87a6a40cd16https://doi.org/10.1021/acs.orglett.6c01509
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