4.8 Article

Pd(II)-Catalyzed Intermolecular Direct C-H Bond Iodination: An Efficient Approach toward the Synthesis of Axially Chiral Compounds via Kinetic Resolution

Journal

ACS CATALYSIS
Volume 4, Issue 8, Pages 2741-2745

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/cs500813z

Keywords

axial chirality; iodination; kinetic resolution; N-oxide; Pd(II)-catalyzed

Funding

  1. National Basic Research Program of China (973 Program) [2010CB833300]
  2. National Natural Science Foundation of China [21025209, 21121062, 21272253, 21332009]

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An efficient protocol to synthesize axially chiral compounds via kinetic resolution by Pd(II)-catalyzed direct C H iodination was realized (up to s = 27). The iodide product could be easily transformed to aryl-substituted pyridine N-oxides via the Suzuki Miyaura coupling, which proved to be a suitable catalyst in asymmetric allylation of benzaldehyde with allyltrichlorosilane.

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