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

文献情報

出版日 2018-09-24

DOI 10.1039/C8OB02161A

インパクトファクター 3.876

著者

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

原文を見る

要旨

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.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

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.

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

文献情報

おすすめジャーナル

関連文献

Cu-catalyzed stereoselective conjugate addition of arylboronic acids to alkynoates

Stabilization of cobalt oxyhydrate superconductor

Macromolecular complexation of poly(methylenephosphine) to gold(i): a facile route to highly metallated polymers

Rapid formation of metal–organic nano-capsules gives new insight into the self-assembly process‡

Contents and Chemical Biology

Improved 3D DOSY-TOCSY experiment for mixture analysis

Fluorescence microscopy coupled to electrochemistry: a powerful tool for the controlled electrochemical switch of fluorescent molecules

Photoinduced CO release, cellular uptake and cytotoxicity of a tris(pyrazolyl)methane (tpm) manganese tricarbonyl complex

A dinuclear ruthenium(ii) complex that functions as a label-free colorimetric sensor for DNA

Back cover

こちらもおすすめ

3-イチチルビフェニルはどのように合成されますか？

8-溴-5-三氟甲基喹啉はどのように合成されますか？

ジメチル4-(4,4,5,5-テトラメチル-1,3,2-ドioxaborolan-2-基)-2,6-ピリジンジカルボイル酸フェニルアミニドの代替品はありますか？

N-(3,5-ヘキサクロロ-4-ピリドインイル)-8-メチオキシ-5-キノリンカーボン酸の市場動向や研究トレンドはどのようなものでしょうか？

イソステアロイルグリセリルは安全ですか？

1-(二苯甲基)-3,3-二氟-氮杂环丁烷の市場動向や研究トレンドはどうですか？

3-チオフェンスチオールの物理化学的性質は何ですか？

2-Methyl-2-propanyl (2S)-2-(aminomethyl)-1-piperidinecarboxylateは安全ですか？

CAS番号1316822-90-8の化合物は安全ですか？

Tert-butyl 2-(2-羟基乙基)哌嗪-1-羧酸はどのように保存すればよいですか？

掲載誌

Organic & Biomolecular Chemistry

おすすめ化合物

Fenofibrate-d6

(2R)-2-(3-Bromophenyl)pyrrolidine hydrochloride (1:1)

5-Iodo-4,6-dimethyl-2-pyrimidinamine

1,4-Bis(bromomethyl)-2,5-dichlorobenzene

tert-Butyl 4-cyanophenethylcarbamate

おすすめサプライヤー