![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)
Sequential and iterative Pd-catalyzed cross-coupling reactions in organic synthesis
Patrick Dobrounig1, Melanie Trobe1, Rolf Breinbauer1
1Institute of Organic Chemistry, Graz University of Technology, Graz, Austria.
Monatshefte Fur Chemie
|January 28, 2017
Summary
This review covers sequential and iterative palladium-catalyzed cross-coupling reactions. Strategies controlling carbon-carbon bond formation order enable precise assembly of complex molecules like oligoarenes.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Palladium-catalyzed cross-coupling reactions are fundamental in organic synthesis.
- Controlling the sequence of multiple bond formations in a single molecule is challenging.
Purpose of the Study:
- To provide an overview of recent advancements in sequential and iterative Pd-catalyzed cross-coupling reactions.
- To highlight strategies for controlling the order of C-C bond formation.
- To discuss the synthesis of oligoarenes and -alkenes.
Main Methods:
- Utilizing substrates with attenuated leaving groups for selective reactivity.
- Employing specific palladium catalyst and ligand combinations to direct reaction pathways.
- Reviewing literature on sequential and iterative cross-coupling methodologies.
Main Results:
- Demonstration of controlled C-C bond formation through substrate or catalyst design.
- Successful assembly of complex oligoarene and oligoalkene structures.
- Overview of diverse strategies enabling sequential coupling.
Conclusions:
- Sequential and iterative cross-coupling reactions offer powerful control over molecular assembly.
- Attenuated leaving groups and tailored catalyst systems are key to achieving selectivity.
- These methods advance the synthesis of complex conjugated organic materials.
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