Rapid C-H bond activation by a monocopper(III)-hydroxide complex

J Am Chem Soc. 2011 Nov 9;133(44):17602-5. doi: 10.1021/ja207882h. Epub 2011 Oct 17.

Abstract

One-electron oxidation of the tetragonal Cu(II) complex [Bu(4)N][LCuOH] at -80 °C generated the reactive intermediate LCuOH, which was shown to be a Cu(III) complex on the basis of spectroscopy and theory (L = N,N'-bis(2,6-diisopropylphenyl)-2,6-pyridinedicarboxamide). The complex LCuOH reacts with dihydroanthracene to yield anthracene and the Cu(II) complex LCu(OH(2)). Kinetic studies showed that the reaction occurs via H-atom abstraction via a second-order rate law at high rates (cf. k = 1.1(1) M(-1) s(-1) at -80 °C, ΔH(‡) = 5.4(2) kcal mol(-1), ΔS(‡) = -30(2) eu) and with very large kinetic isotope effects (cf. k(H)/k(D) = 44 at -70 °C). The findings suggest that a Cu(III)-OH moiety is a viable reactant in oxidation catalysis.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Copper / chemistry*
  • Crystallography, X-Ray
  • Hydroxides / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemistry*

Substances

  • Hydroxides
  • Organometallic Compounds
  • Copper
  • hydroxide ion