Trifluoromethylation and pentafluorophenylation of enamines

被引:11
作者
Dilman, A. D. [1 ]
Gorokhov, V. V. [1 ]
Belyakov, P. A. [1 ]
Struchkova, M. I. [1 ]
Tartakovsky, V. A. [1 ]
机构
[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia
关键词
silanes; iminium cations; pentacoordinate silicon; amines; enamines; organosilicon compounds; organofluorine compounds;
D O I
10.1007/s11172-007-0235-5
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A reaction of enamines with Me3SiCF3 and Me3SiC6F5 in the presence of carboxylic acids leading to alpha-CF3- and alpha-C6F5-substituted amines has been studied. 3-Cyanobenzoic acid was found to be the optimal promoter of these reactions.
引用
收藏
页码:1522 / 1525
页数:4
相关论文
共 18 条
[1]   IMPROVED TITANIUM TETRACHLORIDE PROCEDURE FOR ENAMINE SYNTHESIS .2. SCOPE OF THE REACTION [J].
CARLSON, R ;
NILSSON, A .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (01) :49-53
[2]   Reactions of salicylaldehyde with tris(pentafluorophenyl)silanes and secondary amines [J].
Dilman, A. D. ;
Arkhipov, D. E. ;
Belyakov, P. A. ;
Struchkova, M. I. ;
Tartakovsky, V. A. .
RUSSIAN CHEMICAL BULLETIN, 2006, 55 (03) :517-522
[3]   Synthesis of C6F5-substituted amines containing quaternary carbon atoms [J].
Dilman, AD ;
Levin, VV ;
Belyakov, PA ;
Struchkova, MI ;
Tartakovsky, VA .
SYNTHESIS-STUTTGART, 2006, (03) :447-450
[4]   Synthesis of pentafluorophenylmethylamines via silicon Mannich reaction [J].
Dilman, AD ;
Belyakov, PA ;
Korlyukov, AA ;
Struchkova, MI ;
Tartakovsky, VA .
ORGANIC LETTERS, 2005, 7 (14) :2913-2915
[5]   Activation of pentafluorophenylsilanes by weak Lewis bases in reaction with iminium cations [J].
Dilman, Alexander D. ;
Levin, Vitalij V. ;
Karni, Miriam ;
Apeloig, Yitzhak .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (19) :7214-7223
[6]  
EABORN C, 1967, ORGANOMET CHEM, V9, P259
[7]   MECHANISM OF INACTIVATION OF ALANINE RACEMASE BY BETA,BETA,BETA-TRIFLUOROALANINE [J].
FARACI, WS ;
WALSH, CT .
BIOCHEMISTRY, 1989, 28 (02) :431-437
[8]  
HUNIG S, 1973, ORG SYNTH COLL, V5, P808
[9]   (PENTAFLUOROPHENYL)MAGNESIUM CHLORIDE [J].
JUKES, AE ;
GILMAN, H .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1969, 17 (01) :145-&
[10]   Lewis base-catalyzed trifluoromethylation of aldimines with (trifluoromethyl)trimethylsilane [J].
Kawano, Y ;
Fujisawa, H ;
Mukaiyama, T .
CHEMISTRY LETTERS, 2005, 34 (03) :422-423