Preparation of polysubstituted dihydrofurans through a PhI(OAc)2-promoted haloenolcyclization of olefinic dicarbonyl compounds

Literature Information

Publication Date 2018-09-24
DOI 10.1039/C8OB02161A
Impact Factor 3.876
Authors

Ji Liu, Qing-Yun Liu, Xing-Xiao Fang, Gong-Qing Liu, Yong Ling


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Abstract

A metal-free cyclization of olefinic dicarbonyl compounds for the synthesis of various 5-halomethyl-4,5-dihydrofurans is presented. Using (diacetoxyiodo)benzene as the reaction promoter and halotrimethylsilane as the halogen source, the intramolecular haloenolcyclization of the 2-allyl-1,3-dicarbonyl compounds smoothly proceeded, leading to the corresponding 5-halomethyl-4,5-dihydrofurans in good to excellent isolated yields. Moreover, the resulting 5-iodomethyl products could be converted to functionalized furans in almost quantitative yields by treatment with DBU followed by acid-catalyzed rearrangement. The reactions could be carried out on a gram scale and did not require harsh reaction conditions. The good isolated yields, mild conditions, and operational simplicity make this reaction a viable method for the construction of different dihydrofuran and furan structures.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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