Fluorinative ring-opening of cyclopropanes by hypervalent iodine reagents. An efficient method for 1,3-oxyfluorination and 1,3-difluorination

被引:87
作者
Ilchenko, Nadia O. [1 ]
Hedberg, Martin [1 ]
Szabo, Kalman J. [1 ]
机构
[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden
基金
瑞典研究理事会;
关键词
TRIFLUOROMETHYLATION; AMINOFLUORINATION; CARBOFLUORINATION; OXYFLUORINATION; DERIVATIVES; CHEMISTRY; ALKENES; ARENES; MILD;
D O I
10.1039/c6sc03471c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new method is presented for 1,3-difluorination and 1,3-oxyfluorination reactions. The process is based on iodonium mediated opening of 1,1-disubstituted cyclopropanes. The reaction proceeds with high chemo and regioselectivity under mild reaction conditions typically at room temperature in a couple of hours. The reaction probably occurs via electrophilic ring-opening of cyclopropanes.
引用
收藏
页码:1056 / 1061
页数:6
相关论文
共 54 条
[51]   Highly Selective Pd-Catalyzed Intermolecular Fluorosulfonylation of Styrenes [J].
Yuan, Zheliang ;
Wang, Hao-Yang ;
Mu, Xin ;
Chen, Pinhong ;
Guo, Yin-Long ;
Liu, Guosheng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (07) :2468-2471
[52]   Chemistry of Polyvalent Iodine [J].
Zhdankin, Viktor V. ;
Stang, Peter J. .
CHEMICAL REVIEWS, 2008, 108 (12) :5299-5358
[53]   Efficiency Analysis and Mechanism Insight of that Whole-Cell Biocatalytic Production of Melibiose from Raffinose with Saccharomyces cerevisiae [J].
Zhou, Yingbiao ;
Zhu, Yueming ;
Dai, Longhai ;
Men, Yan ;
Wu, Jinhai ;
Zhang, Juankun ;
Sun, Yuanxia .
APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, 2017, 181 (01) :407-423
[54]   Reactions of Cyclopropanes with Potassium Dihaloiodates [J].
Zyk, N. V. ;
Gavrilova, A. Yu. ;
Bondarenko, O. B. ;
Mukhina, O. A. ;
Tikhanushkina, V. N. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 47 (03) :340-354