Premium
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.