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October 23, 2025Angewandte Chemie0 citationsOpen Access

Stereoselective Synthesis of Alkenyl Fluorides and Alkynes by Defluoro Coupling of Trifluoromethyl Arenes

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JRJosé L. Rosario‐CollazoCWCourtney WestlundHKHawa Keita

Key Points

  • Stereoselective synthesis achieves over 98:2 selectivity in alkynes from trifluoromethyl arenes.
  • Products yielded up to 94% from C–C coupling using functional organodiboron reagents.
  • Assessment using defluoro coupling method produces diverse products with practical applications.
  • This method supports efficient construction of complex molecules, enabling multiple transformations.

Abstract

Abstract A practical method for the stereoselective synthesis of tri‐ and tetra‐substituted 1,2‐fluoro‐borylalkenes and alkynes by defluoro / C–C coupling of aryl trifluoromethyl groups is disclosed. Transformations convert simple abundant CF 3 –arenes and multifunctional organodiboron reagents in the presence of a Lewis base activator into coupled products in up to 94% yield and >98:2 Z/E selectivity. Synthetic utility is highlighted by several product transformations that access an array of diverse scaffolds.

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Cite This Study

Rosario‐Collazo et al. (2025) studied this question.

synapsesocial.com/papers/68f9a0eb8ea8f2f37ee94b88https://doi.org/10.1002/ange.202515710
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