Issue 12, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
26 Feb 2018
Accepted
16 Mar 2018
First published
21 Mar 2018

Org. Chem. Front., 2018,5, 1870-1876

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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