1-Phosphabarrelene complexes of palladium and their use in Suzuki-Miyaura coupling reactions

被引：32

作者：

Blug, Matthias ^{[1
]}

Guibert, Clement ^{[1
]}

Le Goff, Xavier-Frederic ^{[1
]}

Mezailles, Nicolas ^{[1
]}

Le Floch, Pascal ^{[1
]}

机构：

[1] Ecole Polytech, CNRS, Lab Heteroelements & Coordinat, F-91128 Palaiseau, France

来源：

CHEMICAL COMMUNICATIONS | 2009年 / 02期

关键词：

N-HETEROCYCLIC CARBENE; ARYL CHLORIDES; ARYLBORONIC ACIDS; INTERNAL ALKENES; CROSS-COUPLINGS; PHOSPHININES; CATALYSTS; LIGANDS; NHC; HYDROFORMYLATION;

D O I：

10.1039/b814886d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A bulky 1-phosphabarrelene, 2, was obtained from the reaction of a phosphinine with benzyne; two palladium complexes of 2 were successfully employed in the Suzuki-Miyaura coupling of several aryl chlorides with phenylboronic acid at a relatively low catalyst loading, and activated aryl chlorides were coupled at room temperature in the absence of strong bases.

引用

页码：201 / 203

页数：3

共 31 条

[1] 1,3,2-Diazaphosphinines: New, versatile precursors of 1,2-azaphosphinines and polyfunctional phosphinines [J].

Avarvari, N ;

LeFloch, P ;

Mathey, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (47) :11978-11979

[2] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[3] Protodesilylation of 2,6-disubstituted silyphosphinines.: Experimental and theoretical study [J].

Blug, Matthias ;

Piechaczyk, Olivier ;

Fustier, Marie ;

Mezailles, Nicolas ;

Le Floch, Pascal .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (08) :3258-3261

[4] Phosphabarrelene-rhodium complexes as highly active catalysts for isomerization free hydroformylation of internal alkenes [J].

Breit, B ;

Fuchs, E .

CHEMICAL COMMUNICATIONS, 2004, (06) :694-695

[5] Chiral phosphabarrelene ligands: Synthesis and evaluation in rhodium-catalyzed asymmetric hydrogenation [J].

Breit, Bernhard ;

Fuchs, Evelyn .

SYNTHESIS-STUTTGART, 2006, (13) :2121-2128

[6] INVESTIGATION OF DONOR-ACCEPTOR INTERACTIONS - A CHARGE DECOMPOSITION ANALYSIS USING FRAGMENT MOLECULAR-ORBITALS [J].

DAPPRICH, S ;

FRENKING, G .

JOURNAL OF PHYSICAL CHEMISTRY, 1995, 99 (23) :9352-9362

[7] Room-temperature activation of aryl chlorides in Suzuki-Miyaura coupling using a [Pd(μ-Cl)Cl(NHC)]2 complex (NHC = N-heterocyclic carbene) [J].

Diebolt, Olivier ;

Braunstein, Pierre ;

Nolan, Steven P. ;

Cazin, Catherine S. J. .

CHEMICAL COMMUNICATIONS, 2008, (27) :3190-3192

[8] A general synthetic route to mixed NHC-phosphane palladium(0) complexes (NHC = N-heterocyclic carbene) [J].

Fantasia, Serena ;

Nolan, Steven P. .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (23) :6987-6993

[9] The nature of the bonding in transition-metal compounds [J].

Frenking, G ;

Fröhlich, N .

CHEMICAL REVIEWS, 2000, 100 (02) :717-774

[10] Phosphabarrelenes as ligands in rhodium-catalyzed hydroformylation of internal alkenes essentially free of alkene isomerization [J].

Fuchs, Evelyn ;

Keller, Manfred ;

Breit, Bernhard .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (26) :6930-6939

← 1 2 3 4 →