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Issue 12, 2018
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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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Article information


Submitted
26 Feb 2018
Accepted
16 Mar 2018
First published
21 Mar 2018

Org. Chem. Front., 2018,5, 1870-1876
Article type
Research Article
Author version available

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, 5, 1870
DOI: 10.1039/C8QO00207J

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