Mg-promoted double silylation of trifluoroacetimidoyl chlorides. A new entry to the fluorinated dianion equivalents

被引：48

作者：

Kobayashi, T ^{[1
]}

Nakagawa, T ^{[1
]}

Amii, H ^{[1
]}

Uneyama, K ^{[1
]}

机构：

[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 23期

关键词：

D O I：

10.1021/ol035528y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Mg(0)/Me3SiCl system was found to be effective for the preparation of a novel fluorinated dianion equivalent. A one-pot reaction sequence involving reductive C-F and C-Cl bond cleavage reactions of trifluoroacetimidoyl chlorides afforded bis-silylated difluoroenamines. Subsequent carbon-carbon bond-forming reactions of the bis(silyl)enamines with two kinds of electrophiles gave a variety of difluorinated imines.

引用

页码：4297 / 4300

页数：4

共 81 条

[1] Pd-catalyzed asymmetric hydrogenation of α-fluorinated iminoesters in fluorinated alcohol:: A new and catalytic enantioselective synthesis of fluoro α-amino acid derivatives [J].

Abe, H ;

Amii, H ;

Uneyama, K .

ORGANIC LETTERS, 2001, 3 (03) :313-315

[2]

Ager D. J., 1987, UMPOLED SYNTHONS, P19

[3] Difluorinated Danishefsky's diene:: A versatile C4 building block for the fluorinated six-membered rings [J].

Amii, H ;

Kobayashi, T ;

Terasawa, H ;

Uneyama, K .

ORGANIC LETTERS, 2001, 3 (20) :3103-3105

[4] Mg0-promoted selective C-F bond cleavage of trifluoromethyl ketones:: a convenient method for the synthesis of 2,2-difluoro enol silanes [J].

Amii, H ;

Kobayashi, T ;

Hatamoto, Y ;

Uneyama, K .

CHEMICAL COMMUNICATIONS, 1999, (14) :1323-1324

[5] New C-F bond-cleavage route for the synthesis of octafluoro[2.2]paracyclophane [J].

Amii, H ;

Hatamoto, Y ;

Seo, M ;

Uneyama, K .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21) :7216-7218

[6] Rh(I)-catalyzed coupling cyclization of N-aryl trifluoroacetimidoyl chlorides with alkynes:: One-pot synthesis of fluorinated quinolines [J].

Amii, H ;

Kishikawa, Y ;

Uneyama, K .

ORGANIC LETTERS, 2001, 3 (08) :1109-1112

[7]

Amii H, 2000, SYNTHESIS-STUTTGART, P2001

[8] Palladium-catalyzed tert-butoxycarbonylation of trifluoroacetimidoyl iodides [J].

Amii, H ;

Kishikawa, Y ;

Kageyama, K ;

Uneyama, K .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3404-3408

[9] Dynamics of bond breaking in ion radicals. Mechanisms and reactivity in the reductive cleavage of carbon-fluorine bonds of fluoromethylarenes [J].

Andrieux, CP ;

Combellas, C ;

Kanoufi, F ;

Saveant, JM ;

Thiebault, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (40) :9527-9540

[10] The generation of difluoroenolates from trifluoroethanol and reproducible syntheses of α,α-difluoro-β-hydroxy ketones [J].

Balnaves, AS ;

Gelbrich, T ;

Hursthouse, MB ;

Light, ME ;

Palmer, MJ ;

Percy, JM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (17) :2525-2535

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