Nickel‐Catalyzed Alkoxy–Alkyl Interconversion with Alkylborane Reagents through C−O Bond Activation of Aryl and Enol Ethers |
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| Authors: | M Sc Lin Guo Dr Xiangqian Liu Christoph Baumann Prof Dr Magnus Rueping |
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| Institution: | 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: | A nickel‐catalyzed alkylation of polycyclic aromatic methyl ethers as well as methyl enol ethers with B‐alkyl 9‐BBN and trialkylborane reagents that involves the cleavage of stable C(sp2)?OMe bonds is described. The transformation has a wide substrate scope and good chemoselectivity profile while proceeding under mild reaction conditions; it provides a versatile way to form C(sp2)?C(sp3) bonds that does not suffer from β‐hydride elimination. Furthermore, a selective and sequential alkylation process by cleavage of inert C?O bonds is presented to demonstrate the advantage of this method. |
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| Keywords: | alkylation alkylboron reagents aromatic methyl ethers C− O activation nickel catalysis |
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