November 14, 2002Angewandte Chemie International Edition
Palladium-Catalyzed Coupling Reactions of Aryl Chlorides
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Overview
Literature review details advances in palladium-catalyzed couplings of aryl chlorides using electron-rich phosphanes and carbenes, demonstrating expanded synthetic utility for organic chemistry.
Key Points
- To review the historical limitations and modern catalytic developments in palladium-catalyzed cross-coupling reactions utilizing accessible and inexpensive aryl chloride substrates.
- Analyzed literature on traditional palladium and triarylphosphane catalytic systems and their reactivity constraints with unactivated aryl chlorides.
- Evaluated post-1998 synthetic methodologies employing bulky, electron-rich phosphane and carbene ligands to facilitate oxidative addition and coupling.
- Established that conventional palladium catalysts are largely ineffective for general aryl chlorides, functioning only on substrates activated by heteroatoms or electron-withdrawing groups.
- Demonstrated that modern catalyst systems incorporating bulky, electron-rich phosphanes or carbenes enable mild, robust, and highly versatile coupling across diverse aryl chlorides.
Cite This Study
Littke et al. (2002) studied this question.