Multifaceted palladium catalysts towards the tandem diboration-arylation reactions of alkenes

Chemistry. 2008;14(34):10648-55. doi: 10.1002/chem.200800931.

Abstract

Novel Pd(2) (6+) compounds have been synthesized in high yield. These compounds and their Pd(2) (4+) counterparts as synthetic precursors mediate the diboration of vinylarenes and aliphatic 1-alkenes, and under mild and basic reaction conditions they produce a variety of 1,2-diboronate esters with excellent conversions and chemoselectivities. The presence of bis(catecholato)diboron (B(2)cat(2)) favours the reduction of Pd(III) to Pd(II), while the catalytic precursor of Pd(II) is transformed into Pd(0)-nanoparticles. An "in situ" catalytic tandem reaction has been designed to transform the diboronate intermediates into the monoarylated product, which after oxidative workup, provides the carbohydroxylated adduct. Eventually, the same catalyst performs both sequences with total conversion from the alkene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Alkenes / chemistry*
  • Boronic Acids / chemistry*
  • Catalysis
  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Particle Size
  • Stereoisomerism
  • Time Factors

Substances

  • Alcohols
  • Alkenes
  • Boronic Acids
  • Organometallic Compounds
  • Palladium