Electrophilic fluorination using a hypervalent iodine reagent derived from fluoride

被引:84
作者
Geary, Gemma C. [1 ]
Hope, Eric G. [1 ]
Singh, Kuldip [1 ]
Stuart, Alison M. [1 ]
机构
[1] Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England
关键词
SELECTIVE FLUORINATION; BETA-KETOESTERS; TRIFLUOROMETHYLATION; SELECTFLUOR; AGENTS; SALTS; BIS(TETRAFLUOROBORATE); FAMILY; HF;
D O I
10.1039/c3cc44792h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The air and moisture stable fluoroiodane 8, readily prepared on a 6 g scale by nucleophilic fluorination of the hydroxyiodane 7 with TREAT-HF, has been used as an electrophilic fluorinating reagent for the first time to monofluorinate 1,3-ketoesters and difluorinate 1,3-diketones in good isolated yields.
引用
收藏
页码:9263 / 9265
页数:3
相关论文
共 31 条
[1]   Fluorinations of α-seleno carboxylic acid derivatives with hypervalent (difluoroiodo)toluene [J].
Arrica, MA ;
Wirth, T .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (02) :395-403
[2]   1-ALKYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE SALTS - A NOVEL FAMILY OF ELECTROPHILIC FLUORINATING AGENTS [J].
BANKS, RE ;
MOHIALDINKHAFFAF, SN ;
LAL, GS ;
SHARIF, I ;
SYVRET, RG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (08) :595-596
[3]   EFFICIENT ELECTROPHILIC FLUORINATION OF BETA-DICARBONYL COMPOUNDS WITH THE SELECTFLUOR REAGENT F-TEDA-BF4 (1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TETRAFLUOROBORATE)) [J].
BANKS, RE ;
LAWRENCE, NJ ;
POPPLEWELL, AL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) :343-344
[4]   Bromoiodinanes with an I(III)-Br bond: preparation, X-ray crystallography and reactivity as electrophilic brominating agents [J].
Braddock, DC ;
Cansell, G ;
Hermitage, SA ;
White, AJP .
CHEMICAL COMMUNICATIONS, 2006, (13) :1442-1444
[5]   Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation [J].
Eisenberger, P ;
Gischig, S ;
Togni, A .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (09) :2579-2586
[6]   Mild electrophilic trifluoromethylation of secondary and primary aryl- and alkylphosphines using hypervalent iodine(III)-CF3 reagents [J].
Eisenberger, Patrick ;
Kieltsch, Iris ;
Armanino, Nicolas ;
Togni, Antonio .
CHEMICAL COMMUNICATIONS, 2008, (13) :1575-1577
[7]   Enantioselective Reformatsky reaction of ethyl iododifluoroacetate with ketones [J].
Fornalczyk, Michal ;
Singh, Kuldip ;
Stuart, Alison M. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (16) :3332-3342
[8]   Synthesis of α-fluoro-β-hydroxy esters by an enantioselective Reformatsky-type reaction [J].
Fornalczyk, Michal ;
Singh, Kuldip ;
Stuart, Alison M. .
CHEMICAL COMMUNICATIONS, 2012, 48 (29) :3500-3502
[9]   Selective fluorination of beta-ketoesters using iodotoluene difluoride and a HF-amine complex [J].
Hara, S ;
Sekiguchi, M ;
Ohmori, A ;
Fukuhara, T ;
Yoneda, N .
CHEMICAL COMMUNICATIONS, 1996, (16) :1899-1900
[10]  
Hintermann L, 2000, ANGEW CHEM INT EDIT, V39, P4359, DOI 10.1002/1521-3773(20001201)39:23<4359::AID-ANIE4359>3.0.CO