Chemistry Reference
In-Depth Information
CHAPTER 5
Ancillary Ligand Design in the
Development of Palladium
Catalysts for Challenging
Selective Monoarylation
Reactions
MARK STRADIOTTO
Department of Chemistry, Dalhousie University, 6274 Coburg Road,
P.O. Box 15000, Halifax, Nova Scotia, Canada B3H 4R2
Email: mark.stradiotto@dal.ca
5.1 Introduction
The development and application of homogeneous transition metal catalysis
has played a key role in revolutionizing modern chemical synthesis,
1
as
acknowledged recently by the awarding of the Nobel Prizes for Chemistry in
2001, 2005 and 2010; the last of these was given in recognition of the
pioneering work of Richard F. Heck,
2
Ei-ichi Negishi
3
and Akira Suzuki
4
in
establishing effective palladium-catalyzed methodologies for the formation
of C-C bonds.
5,6
In the ensuing years, a diversity of complementary
palladium-catalyzed C-C and C-X (X
ΒΌ
N, O, S, etc.) bond-forming protocols
have been developed. Among these, the arylation of NH-containing sub-
strates (i.e., Buchwald-Hartwig amination, BHA)
7-10
and the a-arylation
(AA)
11,12
of carbonyl compounds have emerged as broadly useful C
sp
2
-N and
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