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 [J].

CARLSON, R ;

NILSSON, A .

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 [J].

CHUIT, C ;

CORRIU, RJP ;

REYE, C ;

YOUNG, JC .

CHEMICAL REVIEWS, 1993, 93 (04) :1371-1448

[4] Synthesis and structural characterization of carbon-centered tris(pentafluorophenyl)silyl derivatives [J].

Dilman, AD ;

Arkhipov, DE ;

Korlyukov, AA ;

Ananikov, VP ;

Danilenko, VM ;

Tartakovsky, VA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (16) :3680-3689

[5] 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

[6] MECHANISM OF BASE-CATALYZED DESILYLATIONS OF ARYL-TRIMETHYLSILANES AND HETEROARYLTRIMETHYLSILANES [J].

EFFENBERGER, F ;

SPIEGLER, W .

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 [J].

Kawano, Y ;

Mukaiyama, T .

CHEMISTRY LETTERS, 2005, 34 (07) :894-895

[9] Lewis base-catalyzed trifluoromethylation of aldimines with (trifluoromethyl)trimethylsilane [J].

Kawano, Y ;

Fujisawa, H ;

Mukaiyama, T .

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 [J].

Kim, CY ;

Chang, JS ;

Doyon, JB ;

Baird, TT ;

Fierke, CA ;

Jain, A ;

Christianson, DW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (49) :12125-12134

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