Dimeric ortho-palladated homoveratrylamine as an efficient homogeneous catalyst for copper-free Sonogashira cross-coupling reaction

被引：8

作者：

Hajipour, Abdol R. ^{[1
,2
]}

Rahimi, Hannaneh

Rafiee, Fatemeh

机构：

[1] Isfahan Univ Technol, Dept Chem, Pharmaceut Res Lab, Esfahan 84156, Iran

[2] Univ Wisconsin, Sch Med, Dept Neurosci, Madison, WI 53706 USA

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2012年 / 26卷 / 12期

关键词：

Sonogashira reaction; catalyst; ortho-palladated complex; internal alkynes; HECK REACTION; COMPLEX; TRIBENZYLAMINE; BROMIDES; LIQUID; SYSTEM; CU;

D O I：

10.1002/aoc.2920

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The catalytic activity of ortho-palladated [Pd{C6H2(CH2CH2NH2)-(OMe)2,3,4}(m-Br)]2, a complex of homoveratrylamine in the copper-free Sonogashira coupling reaction has been investigated. This complex is a catalyst that is efficient, stable and non-sensitive to air and moisture in the Sonogashira reaction. In this homogeneous catalytic system, various aryl halides were efficiently coupled with phenylacetylene in mostly moderate to good yields in N-methylpyrrolidone at 100?degrees C under copper-free conditions. Copyright (C) 2012 John Wiley & Sons, Ltd.

引用

页码：727 / 730

页数：4

共 44 条

[1] C(sp2)-C(sp) and C(sp)-C(sp) coupling reactions catalyzed by oxime-derived palladacycles [J].

Alonso, DA ;

Nájera, C ;

Pacheco, MC .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (9-10) :1146-1158

[2] A copper- and amine-free Sonogashira-type coupling procedure catalyzed by oxime palladacycles [J].

Alonso, DA ;

Nájera, C ;

Pacheco, MC .

TETRAHEDRON LETTERS, 2002, 43 (51) :9365-9368

[3]

[Anonymous], 2004, METAL CATALYZED CROS

[4] Palladacyclic and platinacyclic catalysts for the allylation of aldehydes [J].

Bedford, Robin B. ;

Pilarski, Lukasz T. .

TETRAHEDRON LETTERS, 2008, 49 (27) :4216-4219

[5] Mechanistic studies of SCS-Pd complexes used in Heck catalysis [J].

Bergbreiter, DE ;

Osburn, PL ;

Frels, JD .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (01) :172-184

[6]

Bohlmann F., 1973, Naturally occurring acetylenes

[7] Monomeric and dimeric ortho-metallated palladium(II)-imine systems as liquid crystals [J].

Buey, J ;

Espinet, P .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 507 (1-2) :137-145

[8] Poly(aryleneethynylene)s: Syntheses, properties, structures, and applications [J].

Bunz, UHF .

CHEMICAL REVIEWS, 2000, 100 (04) :1605-1644

[9] A simple and efficient copper-free catalytic system based on a palladacycle for the arylation of alkynes [J].

Consorti, CS ;

Flores, FR ;

Rominger, F ;

Dupont, J .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :133-141

[10] Insights into the Heck reaction with PCP pincer palladium(II) complexes [J].

Eberhard, MR .

ORGANIC LETTERS, 2004, 6 (13) :2125-2128

← 1 2 3 4 5 →