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Synthesis 2011(17): 2803-2809
DOI: 10.1055/s-0030-1260131
DOI: 10.1055/s-0030-1260131
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Iron(II) Chloride Catalyzed Alkylation of Propargyl Ethers: Direct Functionalization of an sp³ C-H Bond Adjacent to Oxygen
Further Information
Received
10 May 2011
Publication Date:
21 July 2011 (online)
Publication History
Publication Date:
21 July 2011 (online)
Abstract
Iron(II) chloride catalyzed direct alkylation of sp³ 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
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