4.7 Article

Copper-mediated pentafluoroethylation of organoboronates and terminal alkynes with TMSCF3

Journal

CHEMICAL COMMUNICATIONS
Volume 58, Issue 33, Pages 5156-5159

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc00975g

Keywords

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Funding

  1. National Key Research and Development Program of China [2021YFF0701700]
  2. National Natural Science Foundation of China [21632009]
  3. Key Programs of the Chinese Academy of Sciences [KGZD-EW-T08]
  4. Key Research Program of Frontier Sciences of CAS [QYZDJ-SSW-SLH049]
  5. China Post-doctoral Science Foundation [2020M671273]

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The TMSCF3-derived CuCF2CF3 species has been successfully utilized for the pentafluoroethylation of organoboronates and terminal alkynes. With 1,10-phenanthroline as a ligand, a wide range of (hetero)arylboronates and alkenylboronates can be smoothly pentafluoroethylated under aerobic conditions. Furthermore, terminal alkynes can undergo aerobic cross-coupling with the TMSCF3-derived CuCF2CF3 species without the need for additional ligands.
The TMSCF3-derived CuCF2CF3 species has been successfully applied in pentafluoroethylation of organoboronates and terminal alkynes. By using 1,10-phenanthroline as a ligand, a broad range of (hetero)arylboronates and alkenylboronates were smoothly pentafluoroethylated under aerobic conditions. Furthermore, terminal alkynes can undergo aerobic cross-coupling with the TMSCF3-derived CuCF2CF3 species in the absence of additional ligands.

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