4.8 Article

Palladium-catalyzed remote para-C-H activation of arenes assisted by a recyclable pyridine-based template

Journal

CHEMICAL SCIENCE
Volume 12, Issue 11, Pages 4126-4131

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc07042d

Keywords

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Funding

  1. NSFC [22022111, 22071248, 21871257]
  2. Natural Science Foundation of Fujian Province [2020J02008]
  3. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  4. Youth Innovation Promotion Association of the Chinese Academy of Sciences [2020306]

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An unprecedented pyridine-based para-directing template (DT) assisted, Pd-catalyzed para-C-H alkenylation of three classes of arenes was reported, which allows for easy synthesis and recycling under mild conditions. This method offers a new approach for the rapid construction of para-substituted arenes.
Direct para-selective C-H functionalization of arenes remains a daunting challenge and is still significantly restricted to a few scaffolds. Herein, we report an unprecedented pyridine-based para-directing template (DT) assisted, Pd-catalyzed para-C-H alkenylation of three classes of arenes, i.e. phenylpropanoic acids, 2-phenyl benzoic acids and benzyl alcohols, with a series of alkenes including perfluoroalkenes. Notably, the pyridine-based para-DT could be easily synthesized and readily recycled under mild conditions. These results may find application in rapid construction of para-substituted arenes and stimulate the exploration of novel methods for para-C-H functionalization of arenes.

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