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October 8, 2025Chinese Journal of Chemistry7 citationsOpen Access

Enantio‐ and Diastereoselective Rh(I)‐Catalyzed Defluorinative Arylation of Pentafluoroethyl Alkenes to Access Fluoroalkenes Featuring a Unique F‐ and CF3‐Substituted sp2‐Carbon†

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HTHao TanYTYihan TangGTGavin Chit Tsui

Key Points

  • Fluoroalkenes with unique F and CF3 substituents can be synthesized through rhodium(I) catalysis, enhancing synthetic versatility.
  • Achieved excellent Z/E selectivities and well-defined alkene geometries in the synthesis of tetra- and trisubstituted products.
  • Using 1,1- and 1,2-disubstituted alkenes expands the scope of accessible functionalized fluoroalkenes with potential applications.
  • This method provides a pathway to create chiral compounds featuring stereogenic centers with F and CF3 functionalities.

Abstract

Comprehensive Summary We herein describe an enantio‐ and diastereoselective rhodium(I)‐catalyzed defluorinative arylation of pentafluoroethyl alkenes with arylboronic acids. A new class of previously inaccessible functionalized fluoroalkenes featuring a sp 2 ‐carbon connected to F and CF 3 can be synthesized. Using both 1,1‐ and 1,2‐disubstituted alkene substrates, tetra‐ and trisubstituted fluoroalkene products are obtained in excellent Z / E selectivities with well‐defined alkene geometry. These fluoroalkenes are potential synthons for accessing chiral compounds containing a stereogenic centre with F and CF 3 group.

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Cite This Study

Tan et al. (2025) studied this question.

synapsesocial.com/papers/68e6494525bc5bdb98713aachttps://doi.org/10.1002/cjoc.70284
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