Synthesis of C6F5-substituted amines containing quaternary carbon atoms

被引：15

作者：

Dilman, AD ^{[1
]}

Levin, VV ^{[1
]}

Belyakov, PA ^{[1
]}

Struchkova, MI ^{[1
]}

Tartakovsky, VA ^{[1
]}

机构：

[1] ND Zelinskii Inst Organ Chem, Moscow 119991, Russia

来源：

SYNTHESIS-STUTTGART | 2006年 / 03期

关键词：

amines; enamines; silicon; hypercoordination; tris(pentafluorophenyl)silyl derivatives;

D O I：

10.1055/s-2006-926277

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of enamines and methyltris(pentafluorophenyl)silane in the presence of acetic acid affording C6F5-substituted amines is described. The proposed mechanism features a transfer of the C6F5 group from the five-coordinate silicate intermediate onto an iminium cation resulting in the generation of a quaternary carbon atom in the C-C bond forming event.

引用

页码：447 / 450

页数：4

共 14 条

[1] IMPROVED TITANIUM TETRACHLORIDE PROCEDURE FOR ENAMINE SYNTHESIS .2. SCOPE OF THE REACTION
CARLSON, R
NILSSON, A
[J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (01): : 49 - 53
[2] CHEN QY, 1990, J CHEM RES-S, P268
[3] REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES
CHUIT, C
CORRIU, RJP
REYE, C
YOUNG, JC
[J]. CHEMICAL REVIEWS, 1993, 93 (04) : 1371 - 1448
[4] Synthesis and structural characterization of carbon-centered tris(pentafluorophenyl)silyl derivatives
Dilman, AD
Arkhipov, DE
Korlyukov, AA
Ananikov, VP
Danilenko, VM
Tartakovsky, VA
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (16) : 3680 - 3689
[5] Synthesis of pentafluorophenylmethylamines via silicon Mannich reaction
Dilman, AD
Belyakov, PA
Korlyukov, AA
Struchkova, MI
Tartakovsky, VA
[J]. ORGANIC LETTERS, 2005, 7 (14) : 2913 - 2915
[6] MECHANISM OF BASE-CATALYZED DESILYLATIONS OF ARYL-TRIMETHYLSILANES AND HETEROARYLTRIMETHYLSILANES
EFFENBERGER, F
SPIEGLER, W
[J]. CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (10): : 3872 - 3899
[7] HUNIG S, 1973, ORG SYNTH COLL, V5, P808
[8] Diastereoselective trifluoromethylation of chiral N-(tolylsulfinyl)imines in the presence of Lewis bases
Kawano, Y
Mukaiyama, T
[J]. CHEMISTRY LETTERS, 2005, 34 (07) : 894 - 895
[9] Lewis base-catalyzed trifluoromethylation of aldimines with (trifluoromethyl)trimethylsilane
Kawano, Y
Fujisawa, H
Mukaiyama, T
[J]. CHEMISTRY LETTERS, 2005, 34 (03) : 422 - 423
[10] Contribution of fluorine to protein-ligand affinity in the binding of fluoroaromatic inhibitors to carbonic anhydrase II
Kim, CY
Chang, JS
Doyon, JB
Baird, TT
Fierke, CA
Jain, A
Christianson, DW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (49) : 12125 - 12134

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