Iron(II) Chloride Catalyzed
Alkylation of Propargyl Ethers: Direct Functionalization
of an sp³ C-H Bond Adjacent to Oxygen

Yongju Xie; Ming Yu; Yuhong Zhang

doi:10.1055/s-0030-1260131

PAPER

Iron(II) Chloride Catalyzed Alkylation of Propargyl Ethers: Direct Functionalization of an sp^³ C-H Bond Adjacent to Oxygen

Yongju Xie^a, Ming Yu^a, Yuhong Zhang*^a,b
^a Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
Fax: +86(571)87953244; e-Mail: yhzhang@ zju.edu.cn;
^b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China

Abstract

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Abstract

Iron(II) chloride catalyzed direct alkylation of sp^³ C-H bond adjacent to oxygen in propargyl ethers has been accomplished by the use of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant under mild reaction conditions. The reaction proceeded smoothly with a variety of 1,3-diketones leading to β-dicarbonyl ether in moderate yields. In the absence of 1,3-diketones, ynenones were produced by the use of iron(III) chloride and DDQ.

Key words

alkylation - iron-catalyzed - propargyl ether - C-H functionalization - C-C bond formation

Full Text

References

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Supplementary Material

Supporting Information

Iron(II) Chloride Catalyzed Alkylation of Propargyl Ethers: Direct Functionalization of an sp³ C-H Bond Adjacent to Oxygen

Iron(II) Chloride Catalyzed Alkylation of Propargyl Ethers: Direct Functionalization of an sp^³ C-H Bond Adjacent to Oxygen