A valuable, inexpensive CuIN-heterocyclic carbene catalyst for the selective diboration of styrene

Vanesa Lillo, Manuel R. Fructos, Jesús Ramirez, Ataualpa A.C. Braga, Feliu Maseras, M. Mar Díaz-Requejo, Pedro J. Pérez, Elena Fernández

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124 Citations (Scopus)

Abstract

The complexes [Cu(NHC)(NCMe)]BF4 (NHC = N-heterocyclic ligand), with bis(catecholato)diboron (B2(cat)2) as the boron source, efficiently catalyze the diboration of styrene with very high degrees of conversion. With the appropriate NHC ligand, the reaction proceeds quantitatively toward the diborated derivative PhCH(Bcat)-CH2(Bcat). The [styrene]/[B2(cat)2] ratio also has a strong effect on the selectivity: the use of an excess of styrene allows modification of the selectivity toward the formation solely of the monoborated derivative. PhCH 2-CH2(Bcat). DFT calculations suggest that no oxidative addition processes take place at copper, hut that intermediates containing coordinated σ-bonds are involved in the catalytic cycle. © 2007 Wiley-VCH Verlag GmhH & Co. KGaA.
Original languageEnglish
Pages (from-to)2614-2621
JournalChemistry - A European Journal
Volume13
Issue number9
DOIs
Publication statusPublished - 26 Jun 2007

Keywords

  • Boranes
  • Boron
  • Copper
  • Nitrogen heterocycles
  • Reaction mechanisms

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