4.8 Article

Facile synthesis of axially chiral styrene-type carboxylic acids via palladium-catalyzed asymmetric C-H activation

期刊

CHEMICAL SCIENCE
卷 12, 期 10, 页码 3726-3732

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc06661c

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资金

  1. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  2. National Science Foundation of China [21971228, 21772187, 21602213]

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A novel method for facile synthesis of axially chiral styrene-type carboxylic acids has been developed, demonstrating excellent yield, stereocontrol, and substrate scope. The produced axially chiral styrene-type carboxylic acids have shown potential as chiral ligands or catalysts in asymmetric synthesis, as successfully applied in Cp*Co-III-catalyzed asymmetric C-H activation reactions.
A novel method by a one-step introduction of axial chirality and sterically hindered group has been developed for facile synthesis of axially chiral styrene-type carboxylic acids. With the palladium-catalyzed C-H arylation and olefination of readily available cinnamic acid established, this transformation demonstrated excellent yield, excellent stereocontrol (up to 99% yield and 99% ee), and broad substrate scope under mild conditions. The axially chiral styrene-type carboxylic acids produced have been successfully applied to Cp*Co-III-catalyzed asymmetric C-H activation reactions, indicating their potential as chiral ligands or catalysts in asymmetric synthesis.

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