Chemistry Reference
In-Depth Information
CHAPTER 2
Carbon-Carbon Bond Forming
by Ball Milling
KATHARINA JACOB, ROBERT SCHMIDT AND ACHIM STOLLE*
Institute for Technical Chemistry and Environmental Chemistry, Friedrich-
Schiller University Jena, Lessingstr 12, D-07743 Jena, Germany
*Email: Achim.Stolle@uni-jena.de
2.1 Introduction
The formation of carbon-carbon bonds is an important field in organic
chemistry. Essential compounds like diphenylacetylene or biphenyl deriva-
tives can be produced that find application in medicine, drug design, elec-
tronics (LCDs (liquid crystal displays), semiconductors) andmanymore areas.
Mechanochemical techniques are widely common in inorganic com-
minution and alloying but in recent years they have received attention in
organic syntheses, too. The application to organic reactions has been
described in several reviews.
1-6
Thereby, the scope of organic reactions
performed under mechanochemical conditions is manifold and reaches
from metal catalyzed cross-coupling reactions to organocatalytic asymmetric
reactions.
Bolm and co-workers have demonstrated for different carbon-carbon
bond forming reactions, like Aldol or Baylis-Hillman reactions, the advan-
tages of ball milling compared to microwave- or ultrasound-assisted syn-
thetic routes.
6
Compared to classic syntheses, reactions performed with
these techniques often require shorter reaction times and previously un-
known molecular transformations have been reported.
7
Furthermore,
reactions in ball mills can be performed solvent-free while in the case of
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