Direct Assembly of Polysubstituted Furans via C( sp  3 )−H Bond Functionalization by Using Dimethyl Sulfoxide as a Dual Synthon | Zendy

Liu Yufeng | Zendy; Hu Yuqun | Zendy; Cao Zhongzhong | Zendy; Zhan Xi | Zendy; Luo Weiping | Zendy; Liu Qiang | Zendy; Guo Cancheng | Zendy

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Direct Assembly of Polysubstituted Furans via C( sp 3 )−H Bond Functionalization by Using Dimethyl Sulfoxide as a Dual Synthon

Author(s) -

Liu Yufeng,

Hu Yuqun,

Cao Zhongzhong,

Zhan Xi,

Luo Weiping,

Liu Qiang,

Guo Cancheng

Publication year - 2019

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201801429

Subject(s) - synthon , chemistry , surface modification , sulfoxide , aryl , triple bond , dimethyl sulfoxide , combinatorial chemistry , medicinal chemistry , organic chemistry , double bond , alkyl

An unusual I 2 ‐mediated triple C( sp 3 )−H functionalization reaction between aryl methyl ketones and dimethyl sulfoxide to form polysubstituted furans has been developed. In this transformation, dimethyl sulfoxide functions as a dual synthon via C( sp 3 )−H functionalization with formation of two C−C bonds, one C−O bond, and one C−S bond in a one‐step process. Iodine is crucial as promoter of the reaction, by which a number of ketones could be converted easily into 2,4,5‐trisubstituted furans. This provides an extremely simple and expeditious approach to high‐value‐added, biologically significant O‐heterocycles. Based on preliminary experiments, a plausible mechanism is proposed.

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