Biomedical Engineering Reference
In-Depth Information
3
METAL-CATALYZED
C-HETEROATOM
CROSS-COUPLING REACTIONS
CHAPTER
RENATA MARCIA DE FIGUEIREDO and JEAN MARC
CAMPAGNE
Institut Charles Gerhardt Montpellier, UMR 5253 CNRS-UM2-UM1-ENSCM,
Ecole Nationale Sup´rieure de Chimie, Montpellier, France
DAMIEN PRIM
Universit´ Versailles-St-Quentin-en-Yvelines, Institut Lavoisier de Versailles UMR
CNRS 8180, Versailles, France
3.1. GENERAL INTRODUCTION
Cross-coupling defines the reaction of carbon or heteroatom nucleophiles with aryl,
vinyl (or alkyl in some instances), and halides (or pseudohalides) with transitionmetal
catalysts [1]. It can be seen as a reaction between an electrophilic and a nucleophilic
reagent with concomitant formation of a
-bond, and thus in amore general definition,
cross-coupling reaction can be considered as a nucleophilic substitution. Over the
years, a cornerstone set of reactions that stands out of such transformation has paved
theway to the emergence of new synthetic disconnections and consequently gave very
useful solutions to long-standing challenges in organic chemistry. Catalytic systems
for palladium cross-coupling reactions (Suzuki (boron mediated) [2], Negishi (zinc
mediated) [3], Corriu-Kumada-Tamao (magnesium mediated) [4], Stille (tin medi-
ated) [5], and Sonogashira (copper mediated) [6]) and carbopalladation (Heck) [7]
are among the most relevant ones for the carbon-carbon (C-C) bond formation. The
extension of such crucial coupling reactions allowing heteroatom introduction has
been followed by the Buchwald-Hartwig (palladium-mediated) [8] and the modern
variation of the Ullmann-Goldberg (copper-mediated) [9] type reactions.
In the past decade, newly developedmetal complexes and ligands have expanded
the scope and the practicality of these transformations and made them a powerful tool
in academic and industrial research. Generally, cross-coupling reactions are related to
s
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