Synthesis of β-organotelluro vinylphosphine oxides by hydrotelluration of 1-alkynylphosphine oxides and their palladium-catalyzed cross-coupling with alkynes

被引：42

作者：

Braga, AL ^{[1
]}

Vargas, F ^{[1
]}

Zeni, G ^{[1
]}

Silveira, CC ^{[1
]}

de Andrade, LH ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 24期

关键词：

phosphine oxide; tellurium; enyne; palladium; cross-coupling;

D O I：

10.1016/S0040-4039(02)00778-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Organotelluro vinylphosphine oxides 2 can be prepared by treatment of 1-alkynylphosphine oxides I with tellurolate anions in satisfactory yields. Compound 2d undergoes direct coupling reaction with terminal alkynes in the presence of PdCl2/CuI, triethylamine and methanol at room temperature to give beta-alkynyl vinylphosphine oxides 3 with retention of configuration in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：4399 / 4402

页数：4

共 47 条

[1] Phosphine oxides as ligands in the hydroformylation reaction [J].

AbuGnim, C ;

Amer, I .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 516 (1-2) :235-243

[2] Weakly ligated palladium complexes PdCl2(RCN)2 in piperidine:: versatile catalysts for Sonogashira reaction of vinyl chlorides at room temperature [J].

Alami, M ;

Crousse, B ;

Ferri, F .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) :114-123

[3] AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL CHLORIDES WITH TERMINAL ACETYLENES [J].

ALAMI, M ;

LINSTRUMELLE, G .

TETRAHEDRON LETTERS, 1991, 32 (43) :6109-6112

[4]

Alami M, 2000, SYNTHESIS-STUTTGART, P1499

[5]

ALEXAKIS A, 1979, SYNTHESIS-STUTTGART, P826

[6] Diastereoselective nucleophilic additions to vinyl phosphine oxides [J].

Bartels, B ;

Clayden, J ;

Martín, CG ;

Nelson, A ;

Russell, MG ;

Warren, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (13) :1807-1822

[7]

Braga A.L, 2001, PHOSPORUS SULFUR SIL, V172, P181

[8] 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

[9] 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

[10]

Braga AL, 2001, SYNLETT, P371

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