Synthesis of α,α-difluorobenzoyl oxygen heterocycles via the radical reaction of 2-iodo-2,2-difluoroacetophenones with unsaturated acids or unsaturated alcohols

被引:18
作者
Chen, Heng [1 ]
Wang, Jiexiong [1 ]
Wu, Jingjing [1 ,2 ]
Kuang, Yujia [1 ]
Wu, Fanhong [1 ]
机构
[1] Shanghai Inst Technol, Sch Chem & Environm Engn, Shanghai 201418, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
alpha-alpha-Difluorobenzoyl oxygen heterocycle; 2-Iodo-2,2-difluoroacetophenone; Radical addition; Unsaturated acids; Unsaturated alcohols; CATALYZED ALPHA-ARYLATION; IODODIFLUOROMETHYL KETONES; PERFLUOROALKYL IODIDES; GAMMA-BUTYROLACTONES; COPPER CATALYST; ARYL BROMIDES; ALKENES; DERIVATIVES; ALKYNES; ARENES;
D O I
10.1016/j.jfluchem.2017.06.003
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A convenient and facile method for the direct synthesis of a,a-difluorobenzoyl lactones or cyclic ethers via the radical cyclization reaction of 2-iodo-2,2-difluoroacetophenone with unsaturated acids or alcohols was reported.
引用
收藏
页码:41 / 46
页数:6
相关论文
共 36 条
[1]  
Adriana L., 2013, CHEM REV, V113, P4567
[2]   Synthesis, structure and pyrolysis of stabilised phosphonium ylides containing saturated oxygen heterocycles [J].
Aitken, R. Alan ;
Karodia, Nazira ;
McCarron, Hollie B. ;
Rouxel, Cecile ;
Sahabo, Nina ;
Slawin, Alexandra M. Z. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (05) :1794-1804
[3]   Synthesis of fluoroalkyl-δ-lactones from polyfluoroalkyl iodides and 5-hexenoic acids [J].
Fang, Xiang ;
Ying, Qi ;
Chen, Yang ;
Yang, Xueyan ;
Yang, Xianjin ;
Wu, Fanhong .
JOURNAL OF FLUORINE CHEMISTRY, 2008, 129 (04) :280-285
[4]   A compound from smoke that promotes seed germination [J].
Flematti, GR ;
Ghisalberti, EL ;
Dixon, KW ;
Trengove, RD .
SCIENCE, 2004, 305 (5686) :977-977
[5]   Pd-Catalyzed α-Arylation of Trimethylsilyl Enolates of α,α-Difluoroacetamides [J].
Ge, Shaozhong ;
Arlow, Sophie I. ;
Mormino, Michael G. ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (41) :14401-14404
[6]   Pd-Catalyzed α-Arylation of α,α-Difluoroketones with Aryl Bromides and Chlorides. A Route to Difluoromethylarenes [J].
Ge, Shaozhong ;
Chaladaj, Wojciech ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (11) :4149-4152
[7]   FLUORO KETONE INHIBITORS OF HYDROLYTIC ENZYMES [J].
GELB, MH ;
SVAREN, JP ;
ABELES, RH .
BIOCHEMISTRY, 1985, 24 (08) :1813-1817
[8]   ADDITION OF PERFLUOROALKYL IODIDES TO 4-PENTENOL AND ITS DERIVATIVES - ONE-POT PREPARATION OF 2-[(F-ALKYL)METHYL]-TETRAHYDROFURANS [J].
GREINER, J ;
MILIUS, A ;
RIESS, JG .
JOURNAL OF FLUORINE CHEMISTRY, 1992, 56 (03) :285-293
[9]   Palladium catalyzed direct α-arylation of α,α-difluoroketones with aryl bromides [J].
Guo, Chen ;
Wang, Ruo-Wen ;
Qing, Feng-Ling .
JOURNAL OF FLUORINE CHEMISTRY, 2012, 143 :135-142
[10]   Evaluation of Difluoromethyl Ketones as Agonists of the γ-Aminobutyric Acid Type B (GABAB) Receptor [J].
Han, Changho ;
Salyer, Amy E. ;
Kim, Eun Hoo ;
Jiang, Xinyi ;
Jarrard, Rachel E. ;
Powers, Matthew S. ;
Kirchhoff, Aaron M. ;
Salvador, Tolani K. ;
Chester, Julia A. ;
Hockerman, Gregory H. ;
Colby, David A. .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (06) :2456-2465