(N-Heterocyclic Carbene)PdCl2(TEA) Complexes: Studies on the Effect of the "Throw-Away" Ligand in Catalytic Activity

被引：135

作者：

Chen, Ming-Tsz ^{[1
]}

Vicic, David A. ^{[1
]}

Turner, Michael L. ^{[2
]}

Navarro, Oscar ^{[1
]}

机构：

[1] Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96825 USA

[2] Univ Manchester, Sch Chem, Organ Mat Innovat Ctr, Manchester M13 9PL, Lancs, England

来源：

ORGANOMETALLICS | 2011年 / 30卷 / 18期

基金：

美国国家科学基金会; 英国工程与自然科学研究理事会;

关键词：

N-HETEROCYCLIC CARBENE; CROSS-COUPLING REACTIONS; ARYL CHLORIDES; (NHC)PD(ALLYL)CL NHC; ARYLBORONIC ACIDS; PEPPSI COMPLEXES; SUZUKI-MIYAURA; PALLADIUM; HALIDES; ACTIVATION;

D O I：

10.1021/om200699p

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis and characterization of a series of (N-heterocyclic carbene)PdCl2(TEA) (TEA = triethylamine) complexes are presented. A comparison of their activity in the Suzuki-Miyaura and Buchwald-Hartwig reactions with similar (N-heterocyclic carbene)Pd(II) complexes is also presented.

引用

页码：5052 / 5056

页数：5

共 34 条

[1] Phosphaadamantanes as ligands for palladium catalyzed cross-coupling chemistry:: Library synthesis, characterization, and screening in the Suzuki coupling of alkyl halides and tosylates containing β-hydrogens with boronic acids and alkylboranes [J].

Brenstrum, T ;

Gerristma, DA ;

Adjabeng, GM ;

Frampton, CS ;

Britten, J ;

Robertson, AJ ;

McNulty, J ;

Capretta, A .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (22) :7635-7639

[2] Density Functional Theory Investigation of the Alkyl-Alkyl Negishi Cross-Coupling Reaction Catalyzed by N-Heterocyclic Carbene (NHC)-Pd Complexes [J].

Chass, Gregory A. ;

O'Brien, Christopher J. ;

Hadei, Niloufar ;

Kantchev, Eric Assen B. ;

Mu, Wei-Hua ;

Fang, De-Cai ;

Hopkinson, Alan C. ;

Csizmadia, Imre G. ;

Organ, Michael G. .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (17) :4281-4288

[3]

CHODKIEWICZ W, 1955, CR HEBD ACAD SCI, V241, P1055

[4]

de Meijere A., 2004, MetalCatalyzed CrossCoupling Reactions, V1

[5] Mixed Phosphite/N-Heterocyclic Carbene Complexes: Synthesis, Characterization and Catalytic Studies [J].

Diebolt, Olivier ;

Jurcik, Vaclav ;

da Costa, Rosenildo Correa ;

Braunstein, Pierre ;

Cavallo, Luigi ;

Nolan, Steven P. ;

Slawin, Alexandra M. Z. ;

Cazin, Catherine S. J. .

ORGANOMETALLICS, 2010, 29 (06) :1443-1450

[6] PALLADIUM CATALYZED SYNTHESIS OF ARYL, HETEROCYCLIC AND VINYLIC ACETYLENE DERIVATIVES [J].

DIECK, HA ;

HECK, FR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :259-263

[7] A highly active catalyst for Pd-catalyzed amination reactions: Cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides [J].

Fors, Brett P. ;

Watson, Donald A. ;

Biscoe, Mark R. ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) :13552-+

[8] syn-1,2-amino alcohols via diastereoselective allylic C-H amination [J].

Fraunhoffer, Kenneth J. ;

White, M. Christina .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (23) :7274-+

[9] Suzuki-Miyaura cross-coupling reactions mediated by palladium/imidazolium salt systems [J].

Grasa, GA ;

Viciu, MS ;

Huang, JK ;

Zhang, CM ;

Trudell, ML ;

Nolan, SP .

ORGANOMETALLICS, 2002, 21 (14) :2866-2873

[10] Differentiating C-Br and C-Cl Bond Activation by Using Solvent Polarity: Applications to Orthogonal Alkyl-Alkyl Negishi Reactions [J].

Hadei, Niloufar ;

Achonduh, George T. ;

Valente, Cory ;

O'Brien, Christopher J. ;

Organ, Michael G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (17) :3896-3899

← 1 2 3 4 →