Chemistry Reference
In-Depth Information
CHAPTER 11
Stereospecific and
Stereoselective Suzuki-Miyaura
Cross-Coupling Reactions
BEN W. GLASSPOOLE, ERIC C. KESKE AND
CATHLEEN M. CRUDDEN*
Department of Chemistry, Queen's University, Kingston, Ontario, Canada
K7L 3N6
*Email: cathleen.crudden@chem.queensu.ca
11.1 Introduction
The Suzuki-Miyaura reaction
1-3
has changed the way in which certain classes
of molecules are made, and in the process it has become one of the most
often employed reactions for carbon-carbon bond formation in the
pharmaceutical industry.
4
Among all other cross-coupling reactions, the
Suzuki-Miyaura reaction stands out for its mildness and low environmental
impact since it does not employ any toxic main group species, can even be
performed in water, open to air and with parts per billion loadings of Pd.
3,5
Despite its obvious broad utility, until recently, the Suzuki-Miyaura reaction
was virtually unheard of for the coupling of stereochemistry-bearing
C-C bonds with the exception of cyclopropyl systems (Scheme 11.1).
6,7
Considering the ubiquity of the transformation and the importance of
chiral molecules to the pharmaceutical industry specifically and organic
chemistry in general, this is a remarkable statement.
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