4.5 Article

Iron-Catalyzed pi-Activated C-O Ether Bond Cleavage with C-C and C-H Bond Formation

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 3, Pages 498-501

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301372

Keywords

Synthetic methods; Allylation; C-O activation; C-C coupling; Hydrogen transfer; Iron

Funding

  1. National Natural Science Foundation of China (NSFC) [21162013]
  2. Beijing National Laboratory for Molecular Sciences (BNLMS)

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A novel and efficient allylic alkylation reaction between -activated ethers and allylsilane was realized under mild conditions through iron(III)-catalyzed Csp3-O ether bond cleavage. The present protocol provides an attractive approach for the construction of sp(3)-sp(3) C-C bonds and can be potentially applied for the selective reduction of benzyl and allyl ethers to their corresponding hydrocarbon compounds by using triethylsilane as a hydride-transfer reagent.

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