Ullmann Coupling MPharm Advanced Organic Chemistry Pablos Chemistry

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The Ullmann Coupling reaction is a powerful method in organic chemistry used to form carbon-carbon bonds between aryl halides (commonly, bromides or iodides) in the presence of a copper catalyst. This reaction is named after its discoverer, Fritz Ullmann. • Mechanism: • 1. **Oxidative Addition**: The reaction begins with the oxidative addition of the aryl halide to the copper catalyst. This step involves breaking the carbon-halogen bond, resulting in the formation of an aryl-copper intermediate and a halide ion. • 2. **Transmetalation**: A second aryl halide molecule coordinates with the aryl-copper species, leading to a transmetalation event where the copper atom exchanges its coordination sphere from one aryl group to the other. This process creates a new aryl-copper intermediate and regenerates the copper catalyst. • 3. **Reductive Elimination**: In this step, the carbon-carbon bond forms, accompanied by the expulsion of a halide ion. The result is the desired coupled product and the regeneration of the copper catalyst, ready for further cycles. • The Ullmann Coupling is a versatile tool for synthesizing complex organic molecules, especially in the context of pharmaceutical and material science research. It allows chemists to construct intricate structures by connecting aromatic rings, expanding the scope of synthetic 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