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Chemoselective synthesis of aryl(pyridinyl)methanol derivatives through Ni-NIXANTPHOS catalyzed α-arylation and tandem arylation/rearrangement of pyridylmethyl ethers

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Abstract

An efficient synthesis of aryl(pyridyl)-methanol derivatives using a nickel-NIXANTPHOS catalyst is described. Combinations of the Ni-NIXANTPHOS catalyst, solvent, and reaction temperature achieved chemoselective arylation and tandem arylation/rearrangement of pyridylmethyl ethers. A large variety of aryl halides were tolerated (55 examples, up to 96% yield). The scalability of the reaction is demonstrated. The order of the tandem arylation and [1,2]-Wittig rearrangement was probed by comparative studies.

Graphical abstract: Chemoselective synthesis of aryl(pyridinyl)methanol derivatives through Ni-NIXANTPHOS catalyzed α-arylation and tandem arylation/rearrangement of pyridylmethyl ethers

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Publication details

The article was received on 26 Feb 2018, accepted on 16 Mar 2018 and first published on 21 Mar 2018


Article type: Research Article
DOI: 10.1039/C8QO00207J
Citation: Org. Chem. Front., 2018, Advance Article
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    Chemoselective synthesis of aryl(pyridinyl)methanol derivatives through Ni-NIXANTPHOS catalyzed α-arylation and tandem arylation/rearrangement of pyridylmethyl ethers

    Z. Liu, M. Li, B. Wang, G. Deng, W. Chen, B. Kim, H. Zhang, X. Yang and P. J. Walsh, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00207J

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