The Synthesis, Characterization and Dehydrogenation of Sigma-Complexes of BN-Cyclohexanes

Chemistry. 2016 Jan 4;22(1):310-22. doi: 10.1002/chem.201502986. Epub 2015 Nov 25.

Abstract

The coordination chemistry of the 1,2-BN-cyclohexanes 2,2-R2 -1,2-B,N-C4 H10 (R2 =HH, MeH, Me2 ) with Ir and Rh metal fragments has been studied. This led to the solution (NMR spectroscopy) and solid-state (X-ray diffraction) characterization of [Ir(PCy3 )2 (H)2 (η(2) η(2) -H2 BNR2 C4 H8 )][BAr(F) 4 ] (NR2 =NH2 , NMeH) and [Rh(iPr2 PCH2 CH2 CH2 PiPr2 )(η(2) η(2) -H2 BNR2 C4 H8 )][BAr(F) 4 ] (NR2 =NH2 , NMeH, NMe2 ). For NR2 =NH2 subsequent metal-promoted, dehydrocoupling shows the eventual formation of the cyclic tricyclic borazine [BNC4 H8 ]3 , via amino-borane and, tentatively characterized using DFT/GIAO chemical shift calculations, cycloborazane intermediates. For NR2 =NMeH the final product is the cyclic amino-borane HBNMeC4 H8 . The mechanism of dehydrogenation of 2,2-H,Me-1,2-B,N-C4 H10 using the {Rh(iPr2 PCH2 CH2 CH2 PiPr2 )}(+) catalyst has been probed. Catalytic experiments indicate the rapid formation of a dimeric species, [Rh2 (iPr2 PCH2 CH2 CH2 PiPr2 )2 H5 ][BAr(F) 4 ]. Using the initial rate method starting from this dimer, a first-order relationship to [amine-borane], but half-order to [Rh] is established, which is suggested to be due to a rapid dimer-monomer equilibrium operating.

Keywords: amine-borane; catalysis; iridium; phosphine; rhodium.

Publication types

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

MeSH terms

  • Amines / chemistry*
  • Boron Compounds / chemical synthesis*
  • Boron Compounds / chemistry*
  • Crystallography, X-Ray
  • Cyclohexanes / chemical synthesis*
  • Cyclohexanes / chemistry*
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Rhodium / chemistry*
  • Stereoisomerism
  • X-Ray Diffraction

Substances

  • Amines
  • Boron Compounds
  • Cyclohexanes
  • Ligands
  • Organometallic Compounds
  • Rhodium