Radical Conjugated Addition: Addition of Dialkyl Phosphonodifluoromethyl Radical onto Unsaturated Ketones

被引:17
作者
Sene, Aboubacary [1 ]
Diab, Sonia [1 ]
Hienzsch, Antje [1 ]
Cahard, Dominique [2 ]
Lequeux, Thierry [1 ]
机构
[1] Univ Caen, ENSICAEN, CNRS, Lab Chim Mol & Thioorgan,UMR 6507 & FR3038, F-14050 Caen, France
[2] Univ Rouen, INSA Rouen, CNRS, UMR 6014 & FR3038, F-76130 Mont St Aignan, France
关键词
radical reaction; fluorine; enone; phosphonate; alkene; ALPHA; ALPHA-DIFLUORO FUNCTIONALIZED PHOSPHONATES; ETHYL BROMODIFLUOROACETATE; DIFLUOROMETHYL RADICALS; GENERAL-METHOD; COPPER-POWDER; ANALOGS; ALKENES; ALKYNES; MIMICS; ACIDS;
D O I
10.1055/s-0028-1088207
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The free radical addition of phosphonodifluoromethyl radical is reported from iodophosphonate and sodium dithionite, triethylborane, or dilauroyl peroxide as initiator. Triethylborane promoted the radical conjugated addition onto enones.
引用
收藏
页码:981 / 985
页数:5
相关论文
共 45 条
[1]   (α-monofluoroalkyl)phosphonates:: a class of isoacidic and "tunable" mimics of biological phosphates [J].
Berkowitz, DB ;
Bose, M .
JOURNAL OF FLUORINE CHEMISTRY, 2001, 112 (01) :13-33
[2]   α-fluorinated phosphonates as substrate mimics for glucose 6-phosphate dehydrogenase:: the CHF stereochemistry matters [J].
Berkowitz, DB ;
Bose, M ;
Pfannenstiel, TJ ;
Doukov, T .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4498-4508
[3]   MONOFLUORO-METHYLENEBISPHOSPHONIC AND DIFLUORO-METHYLENEBISPHOSPHONIC ACIDS - ISOPOLAR ANALOGS OF PYROPHOSPHORIC ACID [J].
BLACKBURN, GM ;
ENGLAND, DA ;
KOLKMANN, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (17) :930-932
[4]   THE SYNTHESIS AND METAL-BINDING CHARACTERISTICS OF NOVEL, ISOPOLAR PHOSPHONATE ANALOGS OF NUCLEOTIDES [J].
BLACKBURN, GM ;
KENT, DE ;
KOLKMANN, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05) :1119-1125
[5]   COMPARATIVE-STUDIES ON THE GENERATION AND CYCLIZATION REACTIONS OF DIFLUOROALKYL RADICALS [J].
BUTTLE, LA ;
MOTHERWELL, WB .
TETRAHEDRON LETTERS, 1994, 35 (23) :3995-3998
[6]   FLUORINE IN ENZYME CHEMISTRY .2. THE PREPARATION OF DIFLUOROMETHYLENEPHOSPHONATE ANALOGS OF GLYCOLYTIC PHOSPHATES - APPROACHING AN ISOSTERIC AND ISOELECTRONIC PHOSPHATE MIMIC [J].
CHAMBERS, RD ;
JAOUHARI, R ;
OHAGAN, D .
TETRAHEDRON, 1989, 45 (16) :5101-5108
[7]   THE DIFLUOROMETHYLENEPHOSPHONATE MOIETY AS A PHOSPHATE MIMIC - X-RAY STRUCTURE OF 2-AMINO-1,1-DIFLUOROETHYLPHOSPHONIC ACID [J].
CHAMBERS, RD ;
OHAGAN, D ;
LAMONT, RB ;
JAIN, SC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (15) :1053-1054
[8]   Pathway for the stereocontrolled Z and E production of α,α-difluorine-substituted phenyl butenoates [J].
Ghattas, Wadih ;
Hess, Corinna R. ;
Iacazio, Gilles ;
Hardre, Renaud ;
Klinman, Judith P. ;
Reglier, Marius .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22) :8618-8621
[9]   Synthesis of fused piperidinones through a radical-ionic cascade [J].
Godineau, Edouard ;
Schenk, Kurt ;
Landais, Yannick .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (18) :6983-6993
[10]   A difluorosulfide as a Freon-free source of phosphonodifluoromethyl carbanion [J].
Henry-dit-Quesnel, A ;
Toupet, L ;
Pommelet, JC ;
Lequeux, T .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (14) :2486-2491