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Lewis acid controlled regioselectivity in styrene hydrocyanation
Laura Bini1, Evgeny A Pidko, Christian Müller
1Schuit Institute of Catalysis, Laboratory for Inorganic Chemistry and Catalysis, Eindhoven University of Technology, 5600 MB Eindhoven, The Netherlands.
Adding Lewis acids dramatically reverses regioselectivity in nickel-catalyzed styrene hydrocyanation, favoring linear products. This discovery enhances control over chemical synthesis pathways.
Area of Science:
- Organometallic Chemistry
- Catalysis
- Organic Synthesis
Background:
- Nickel-catalyzed hydrocyanation typically yields branched products.
- Regioselectivity control is crucial for efficient synthesis.
Purpose of the Study:
- To investigate Lewis acid influence on Ni-catalyzed styrene hydrocyanation regioselectivity.
- To understand the reaction mechanism and predict Lewis acid behavior.
Main Methods:
- Deuterium labeling experiments
- Nuclear Magnetic Resonance (NMR) studies
- Density Functional Theory (DFT) calculations
Main Results:
- Addition of Lewis acids, like aluminum chloride (AlCl3), inverted regioselectivity, yielding up to 83% linear 3-phenylpropionitrile.
- DFT calculations rationalized and predicted the behavior of various Lewis acids, including copper cyanide (CuCN).
Conclusions:
- Lewis acids can effectively control regioselectivity in Ni-catalyzed hydrocyanation.
- The study provides mechanistic insights and predictive capabilities for catalyst design.
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