Reactions of salicylaldehyde with tris(pentafluorophenyl)silanes and secondary amines

被引：11

作者：

Dilman, A. D. ^{[1
]}

Arkhipov, D. E. ^{[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

来源：

RUSSIAN CHEMICAL BULLETIN | 2006年 / 55卷 / 03期

关键词：

pentafluorophenylsilanes; salicylaldehyde; iminium cation; pentacoordinated silicon; organofluorine compounds; amines; organosilicon compounds;

D O I：

10.1007/s11172-006-0285-0

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reactions of tris(pentafluorophenyl)silanes RSi(C6F5)(3) with salicylaldehyde and secondary amines were studied. The reactions afforded (x-pentafluorophenyl-substituted amines. Silanes RSi(C6F5)(3) (R = Me, Ph, C6F5, CH2CH=CH2, and CH=CH2) were found to be efficient reagents for transfer of the C6F5 group to the iminium cation generated from salicylaldehyde and amine. However, tris(pentafluorophenyl)phenylethynyl- and tris(pentafluorophenyl)silanes were not able to serve as a source of a fluorinated substituent because of competitive transfer of acetylenide fragment or hydride.

引用

页码：517 / 522

页数：6

共 14 条

[1] 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

[2] 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

[3] 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

[4] MECHANISM OF INACTIVATION OF ALANINE RACEMASE BY BETA,BETA,BETA-TRIFLUOROALANINE [J].

FARACI, WS ;

WALSH, CT .

BIOCHEMISTRY, 1989, 28 (02) :431-437

[5] FLUORIDE ION-CATALYZED GENERATION AND CARBONYL ADDITION OF ALPHA-HALO CARBANIONS DERIVED FROM ALPHA-HALO ORGANO-SILICON COMPOUNDS [J].

FUJITA, M ;

OBAYASHI, M ;

HIYAMA, T .

TETRAHEDRON, 1988, 44 (13) :4135-4145

[6]

HOSOMI A, 1978, TETRAHEDRON LETT, P3043

[7] 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

[8] Lewis base-catalyzed additions of alkynes using trialkoxysilylalkynes [J].

Lettan, RB ;

Scheidt, KA .

ORGANIC LETTERS, 2005, 7 (15) :3227-3230

[9] Direct access to CF3-propargyl amines and conversion to difluoromethyl imines [J].

Magueur, G ;

Crousse, B ;

Bonnet-Delpon, D .

TETRAHEDRON LETTERS, 2005, 46 (13) :2219-2221

[10]

Prakash GKS, 2001, SYNLETT, P77

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