Intermolecular hydrophosphination of alkynes and related carbon-carbon multiple bonds catalyzed by ytterbium-imine complexes

被引：80

作者：

Takaki, K ^{[1
]}

Takeda, M ^{[1
]}

Koshoji, G ^{[1
]}

Shishido, T ^{[1
]}

Takehira, K ^{[1
]}

机构：

[1] Hiroshima Univ, Dept Chem & Chem Engn, Grad Sch Engn, Higashihiroshima 7398527, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 36期

关键词：

hydrophosphination; lanthanide catalyst; alkynes; alkenylphosphines;

D O I：

10.1016/S0040-4039(01)01280-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic intermolecular hydrophosphination of alkynes with Ph,PH has been achieved by using a ytterbium-imine complex, [Yb(eta (2)-Ph(2)CNPh)(hmpa)(6)]. Thus, both terminal and internal alkynes were converted in high yields to the corresponding alkenylphosphines or phosphine oxides after oxidative workup. The present method was also applicable to various carbon-carbon multiple bonds such as conjugated diynes and dienes, allenes and styrene derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6357 / 6360

页数：4

共 23 条

[1] CONCERNING PHOSPHIRENIUM CATIONS [J].

BRESLOW, R ;

DEURING, LA .

TETRAHEDRON LETTERS, 1984, 25 (13) :1345-1348

[2] Organolanthanide-catalyzed intramolecular hydrophosphination/cyclization of phosphinoalkenes and phosphinoalkynes [J].

Douglass, MR ;

Marks, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) :1824-1825

[3]

GIARDELLO MA, 1992, NATO ADV SCI I C-MAT, V367, P35

[4] Oxidative addition of HP(O)Ph(2) to platinum(0) and palladium(0) complexes and palladium-catalyzed regio- and stereoselective hydrophosphinylation of alkynes [J].

Han, LB ;

Choi, N ;

Tanaka, M .

ORGANOMETALLICS, 1996, 15 (15) :3259-3261

[5]

Han LB, 1998, ANGEW CHEM INT EDIT, V37, P94

[6] Palladium-catalyzed hydrophosphorylation of alkynes via oxidative addition of HP(O)(OR)(2) [J].

Han, LB ;

Tanaka, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (06) :1571-1572

[7] APPROACHES TO WATER-SOLUBLE PHOSPHINES .2. FREE-RADICAL ADDITION-REACTIONS OF PHENYLPHOSPHINES [J].

HEESCHEWAGNER, K ;

MITCHELL, TN .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 468 (1-2) :99-106

[8] STEREOSELECTIVE SYNTHESIS OF VINYLPHOSPHONATE [J].

HIRAO, T ;

MASUNAGA, T ;

OHSHIRO, Y ;

AGAWA, T .

TETRAHEDRON LETTERS, 1980, 21 (37) :3595-3598

[9] PALLADIUM-CATALYZED NEW CARBON-PHOSPHORUS BOND FORMATION [J].

HIRAO, T ;

MASUNAGA, T ;

YAMADA, N ;

OHSHIRO, Y ;

AGAWA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (03) :909-913

[10] PALLADIUM-CATALYZED PHOSPHORYLATION OF ALKENYL TRIFLATES [J].

HOLT, DA ;

ERB, JM .

TETRAHEDRON LETTERS, 1989, 30 (40) :5393-5396

← 1 2 3 →