Stereospecific synthesis of phosphono-(1Z,3E)-dienyl compounds from β-phenyltelluro-vinylphosphonates and -vinylphosphine oxides

被引：15

作者：

Braga, AL ^{[1
]}

Rhoden, CRB ^{[1
]}

Zeni, G ^{[1
]}

Silveira, CC ^{[1
]}

Andrade, LH ^{[1
]}

机构：

[1] Univ Fed Santa Maria, Dept Quim, BR-97105900 Santa Maria, RS, Brazil

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2003年 / 682卷 / 1-2期

关键词：

phosphine oxide; phosphonates; tellurium; dienes; palladium; cross-coupling;

D O I：

10.1016/S0022-328X(03)00671-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Phosphono-1,3-dienyl compounds 2 can be prepared by palladium cross-coupling reaction of beta-phenyltelluro-vinylphosphonates or -vinylphosphine oxides with alkenes in the presence of a catalytic amount of PdCl2 and AcOAg as reoxidant agent at room temperature. The coupling reaction is stereospecific and the compounds 2 were obtained in good yields with total retention of configuration. (C) 2003 Elsevier B.V. All rights reserved.

引用

页码：35 / 40

页数：6

共 30 条

[1] Stereocontrolled synthesis of polyenoic acids by a Heck-Sonogashira reaction:: easy access to 9,10-didehydro retinoic acids [J].

Abarbri, M ;

Thibonnet, J ;

Parrain, JL ;

Duchêne, A .

TETRAHEDRON LETTERS, 2002, 43 (26) :4703-4705

[2] Stereoselective addition of sodium organyl chalcogenolates to alkynylphosphonates: synthesis of diethyl 2-(organyl)-2-(organochalcogenyl)vinylphosphonates [J].

Braga, AL ;

Alves, EF ;

Silveira, CC ;

de Andrade, LH .

TETRAHEDRON LETTERS, 2000, 41 (02) :161-163

[3] Sonogashira cross-coupling reaction of organotellurium dichlorides with terminal alkynes [J].

Braga, AL ;

Lüdtke, DS ;

Vargas, F ;

Donato, RK ;

Silveira, CC ;

Stefani, MA ;

Zeni, G .

TETRAHEDRON LETTERS, 2003, 44 (09) :1779-1781

[4] Synthesis of β-organotelluro vinylphosphine oxides by hydrotelluration of 1-alkynylphosphine oxides and their palladium-catalyzed cross-coupling with alkynes [J].

Braga, AL ;

Vargas, F ;

Zeni, G ;

Silveira, CC ;

de Andrade, LH .

TETRAHEDRON LETTERS, 2002, 43 (24) :4399-4402

[5] Stereospecific formation of enynephosphonates via palladium-catalyzed cross-coupling reaction of β-organotelluro vinylphosphonates with alkynes [J].

Braga, AL ;

de Andrade, LH ;

Silveira, CC ;

Moro, AV ;

Zeni, G .

TETRAHEDRON LETTERS, 2001, 42 (49) :8563-8565

[6] SYNTHESIS AND PROPERTIES OF ADENOSINE OLIGONUCLEOTIDE ANALOGS CONTAINING METHYLENE GROUPS IN-PLACE OF PHOSPHODIESTER 5'-OXYGENS [J].

BREAKER, RR ;

GOUGH, GR ;

GILHAM, PT .

BIOCHEMISTRY, 1993, 32 (35) :9125-9128

[7] SYNTHESIS OF (+-)-ABSCISIN 2 [J].

CORNFORTH, JW ;

MILBORROW, BV ;

RYBACK, G .

NATURE, 1965, 206 (4985) :715-+

[8] Palladium-catalyzed cross-coupling reactions of dimethyl- and diethylzinc with unsaturated organotellurium compounds [J].

Dabdoub, MJ ;

Dabdoub, VB ;

Marino, JP .

TETRAHEDRON LETTERS, 2000, 41 (04) :433-436

[9] Novel and general cross-coupling reactions of alkynylzinc reagents and organotellurium compounds [J].

Dabdoub, MJ ;

Dabdoub, VB ;

Marino, JP .

TETRAHEDRON LETTERS, 2000, 41 (04) :437-440

[10]

DARLING SD, 1979, TETRAHEDRON LETT, P2757

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