4.8 Article

Pd(II)-catalyzed alkoxylation of unactivated C(sp3)-H and C(sp2)-H bonds using a removable directing group: efficient synthesis of alkyl ethers

Journal

CHEMICAL SCIENCE
Volume 4, Issue 11, Pages 4187-4192

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3sc51993g

Keywords

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Funding

  1. National Science Foundation of China [21002087, 21142002, 21272206, J1210042]
  2. Fundamental Research Funds for the Central Universities [2010QNA3033]
  3. Zhejiang Provincial NSFC [Z12B02000]
  4. Qianjiang Project [2013R10033]
  5. Specialized Research Fund for the Doctoral Program of Higher Education [20110101110005]

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The Pd(II)-catalyzed alkoxylation of unactivated C(sp(3))-H and C(sp(2))-H bonds using a new bidentate directing group has been developed. Alkoxylation occurs selectively at the beta position with broad substrate scope and high tolerance of functional groups (chloro, cyano, ether, ester, olefin, amino, etc.). Besides alkoxylation of the beta-C-H bonds, gamma-alkoxylation of C(sp(2))-H bonds could also be achieved, provided that no reactive beta-C-H bonds were present. In addition, this DG is readily available and removable.

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