Lewis Acid Assisted Nickel‐Catalyzed Cross‐Coupling of Aryl Methyl Ethers by C−O Bond‐Cleaving Alkylation: Prevention of Undesired β‐Hydride Elimination |
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| Authors: | M. Sc. Xiangqian Liu Dr. Chien‐Chi Hsiao M. Sc. Indrek Kalvet Dr. Matthias Leiendecker M. Sc. Lin Guo Prof. Dr. Franziska Schoenebeck Prof. Dr. Magnus Rueping |
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| Affiliation: | 1. Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany;2. King Abdullah University of Science and Technology (KAUST), KAUST Catalysis Center (KCC), Thuwal, Saudi Arabia |
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| Abstract: | In the presence of trialkylaluminum reagents, diverse aryl methyl ethers can be transformed into valuable products by C?O bond‐cleaving alkylation, for the first time without the limiting β‐hydride elimination. This new nickel‐catalyzed dealkoxylative alkylation method enables powerful orthogonal synthetic strategies for the transformation of a variety of naturally occurring and easily accessible anisole derivatives. The directing and/or activating properties of aromatic methoxy groups are utilized first, before they are replaced by alkyl chains in a subsequent coupling process. |
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| Keywords: | C− O bond activation C− C cross-coupling cross-coupling nickel trialkylaluminum |
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