Fluorination of sulfides using IF5-Et3N-3HF

被引:26
作者
Ayuba, S [1 ]
Yoneda, N [1 ]
Fukuhara, T [1 ]
Hara, S [1 ]
机构
[1] Hokkaido Univ, Grad Sch Engn, Div Mol Chem, Kita Ku, Sapporo, Hokkaido 0608628, Japan
关键词
D O I
10.1246/bcsj.75.1597
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Mono- and difluorinations of sulfides were achieved using a novel fluorinating reagent, IF5-Et3N-3HF. The reagent is applicable for substrates having various electron-withdrawing groups, such as an ester, amide, ketone, nitrile, sulfone, or trifluoromethyl. Because more than one fluorine atom on IF5 is used, a large excess amount of the reagent is not necessary, even for the difluorination reaction.
引用
收藏
页码:1597 / 1603
页数:7
相关论文
共 39 条
[1]   ETHYL PHENYLSULFINYL FLUOROACETATE, A NEW AND VERSATILE REAGENT FOR THE PREPARATION OF ALPHA-FLUORO-ALPHA,BETA-UNSATURATED CARBOXYLIC-ACID ESTERS [J].
ALLMENDINGER, T .
TETRAHEDRON, 1991, 47 (27) :4905-4914
[2]   Tetrakis(dimethylamino)ethylene (TDAE) mediated addition of difluoromethyl anions to heteroaryl thiocyanates.: A new simple access to heteroaryl-SCF2R derivatives [J].
Billard, T ;
Langlois, BR ;
Médebielle, M .
TETRAHEDRON LETTERS, 2001, 42 (20) :3463-3465
[3]   OXIDATIVE FLUORINATION OF SULFIDES IN PRESENCE OF ET3N.3HF [J].
BRIGAUD, T ;
LAURENT, E .
TETRAHEDRON LETTERS, 1990, 31 (16) :2287-2290
[4]   Synthesis of α-(heteroarylthio)-α,α-difluoroacetophenone derivatives via the SRN1 methodology [J].
Burkholder, C ;
Dolbier, WR ;
Médebielle, M ;
Ait-Mohand, S .
TETRAHEDRON LETTERS, 2001, 42 (20) :3459-3462
[5]   Synthesis and reactivity of halogeno-difluoromethyl aromatics and heterocycles -: Application to the synthesis of gem-difluorinated bioactive compounds [J].
Burkholder, CR ;
Dolbier, WR ;
Médebielle, M .
JOURNAL OF FLUORINE CHEMISTRY, 2001, 109 (01) :39-48
[6]   The syntheses of nonnucleoside, HIV-1 reverse transcriptase inhibitors containing a CF2 group -: The SRN1 reactions of 2-(bromodifluoromethyl)benzoxazole with the anions derived from heterocyclic thiols and phenolic compounds [J].
Burkholder, CR ;
Dolbier, WR ;
Médebielle, M .
JOURNAL OF FLUORINE CHEMISTRY, 2000, 102 (1-2) :369-376
[7]   Electrochemical fluorination of aliphatic aldehydes and cyclic ketones using Et3N-5HF electrolyte [J].
Chen, SQ ;
HAtakeyama, T ;
Fukuhara, T ;
Hara, S ;
Yoneda, N .
ELECTROCHIMICA ACTA, 1997, 42 (13-14) :1951-1960
[8]   ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .13. SELECTIVE ANODIC ALPHA-FLUORINATION OF NITROGEN-CONTAINING HETEROCYCLIC SULFIDES AND ITS APPLICATION TO THE SYNTHESIS OF FLUORINATED FUSED HETEROCYCLES [J].
ERIAN, AW ;
KONNO, A ;
FUCHIGAMI, T .
TETRAHEDRON LETTERS, 1994, 35 (39) :7245-7248
[9]  
Ero H., 2001, CHEM PHARM BULL, V49, P173
[10]   ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .4. REGIOSELECTIVE ANODIC MONOFLUORINATION OF 4-THIAZOLIDINONES AND ITS APPLICATION TO THE SYNTHESIS OF MONOFLUORO BETA-LACTAMS [J].
FUCHIGAMI, T ;
NARIZUKA, S ;
KONNO, A .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3755-3757