4.7 Article

Nickel-Catalyzed Borylation of Aryl and Benzyl 2-Pyridyl Ethers: A Method for Converting a Robust ortho-Directing Group

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 15, Pages 2417-2421

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600336

Keywords

borylation; C-O activation; cross-coupling; directing group; nickel catalyst

Funding

  1. MEXT, Japan
  2. ACT-C from JST, Japan

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The nickel-catalyzed borylation of aryl 2-pyridyl ethers via the loss of a 2-pyridyloxy group is described. This method allows a 2-pyridyloxy group to be used as a convertible directing group in C-H bond functionalization reactions. The nickel catalyst can also borylate arylmethyl 2-pyridyl ethers, in which the stereochemistry at the benzylic position is retained in the case of chiral secondary benzylic substrates.

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