Chemistry Reference
In-Depth Information
CHAPTER 8
Boron Reagent Activation in
Suzuki-Miyaura Coupling
ALASTAIR LENNOX AND GUY LLOYD-JONES*
School of Chemistry, West Mains Road, Edinburgh, EH9 3JJ, UK
*Email: guy.lloyd-jones@ed.ac.uk
8.1
Suzuki-Miyaura Cross-Coupling
8.1.1 Introduction
Over the last two decades, the advent of practical and scalable transition
metal-catalysed cross-coupling reactions has truly revolutionized organic
synthesis. Of the various metals explored, palladium has proven to be
exceptional. A wide variety of Pd complexes and ligands are readily access-
ible or commercially available and there is usually a low thermodynamic
differential between oxidation states, in this case 0 and 2, as required for
ecient turnover in cross-coupling. The propensity for Pd(0) to undergo
oxidative addition to a wide range of organohalides and pseudohalides,
together with the development of a suite of formally nucleophilic coupling
partners, has led to a very broad spectrum of applications in cross-coupling.
One can subdivide the nucleophilic coupling partners into those based on
organic reactants, e.g. alkenes (Heck)
1,2
and alkynes (Sonogashira)
3
and
those based on organometallics or organometalloids, such as magnesium
(Kumada),
4
zinc (Negishi)
5
tin (Stille)
6
silicon (Hiyama)
7
and boron (Suzuki-
Miyaura)
8
(Scheme 8.1). Recognition of these pivotal contributions to the
development of synthetic methods was recently made by the award of
the 2010 Nobel Prize in Chemistry to three of the pioneers in the area.
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