Catalytic Alkynylation of Polyfluoroarenes by Amide Base Generated In Situ

Catalytic Alkynylation of Polyfluoroarenes by Amide Base Generated In Situ

We herein demonstrate that the amide base generated in situ from CsF and N(TMS)3 catalyzes the deprotonative coupling reactions of terminal alkynes with polyfluoroarenes, wherein mono‐ and dialkynylations occur efficiently for penta‐ and hexafluorobenzenes, respectively. Tetraalkynylated products co...

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Veröffentlicht in:Chemistry : a European journal 2019-08, Vol.25 (44), p.10294-10297
Hauptverfasser: Shigeno, Masanori, Okawa, Takuya, Imamatsu, Masaya, Nozawa‐Kumada, Kanako, Kondo, Yoshinori
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes
amide base
aromatic substitution
Catalysis
Cesium fluorides
Chemical reactions
Chemistry
C−C coupling
polyfluoroarenes
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Zusammenfassung:We herein demonstrate that the amide base generated in situ from CsF and N(TMS)3 catalyzes the deprotonative coupling reactions of terminal alkynes with polyfluoroarenes, wherein mono‐ and dialkynylations occur efficiently for penta‐ and hexafluorobenzenes, respectively. Tetraalkynylated products could also be synthesized from dialkynylated compounds. Aromatic substitution: Amide base generated in situ from CsF and N(TMS)3 catalyzes the deprotonative coupling reactions of terminal alkynes with polyfluoroarenes, wherein mono‐ and dialkynylations occur efficiently for penta‐ and hexafluorobenzenes, respectively. Tetraalkynylated products can also be synthesized from dialkynylated compounds (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201901501