Biphenylene-Substituted Ruthenocenylphosphine for Suzuki-Miyaura Coupling of Sterically Hindered Aryl Bromides

被引：32

作者：

Hoshi, Takashi ^{[1
]}

Saitoh, Ippei ^{[2
]}

Nakazawa, Taichi ^{[2
]}

Suzuki, Toshio ^{[1
]}

Sakai, Jun-ichi ^{[1
]}

Hagiwara, Hisahiro ^{[2
]}

机构：

[1] Niigata Univ, Fac Engn, Nishi Ku, Niigata 9502181, Japan

[2] Niigata Univ, Fac Engn, Grad Sch Sci & Technol, Niigata 9502181, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 10期

关键词：

PALLADIUM-CATALYZED AMINATION; HETEROCYCLIC CARBENE LIGANDS; HECK REACTIONS; RESTRICTED FLEXIBILITY; ENOL ETHERS; CHLORIDES; HALIDES; DERIVATIVES; DISCOVERY; ARYLATION;

D O I：

10.1021/jo900550g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly general, active, and stable catalytic system was realized in the palladium-catalyzed Suzuki-Miyaura reactions of sterically hindered aryl bromides with arylboronic acids using biphenylene-substituted di-tert-butylruthenocenylphosphine (R-Phos) as a supporting ligand.

引用

页码：4013 / 4016

页数：4

共 48 条

[1] Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 2: The Suzuki reaction [J].

Alonso, Francisco ;

Beletskaya, Irina P. ;

Yus, Miguel .

TETRAHEDRON, 2008, 64 (14) :3047-3101

[2] Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis [J].

Altenhoff, G ;

Goddard, R ;

Lehmann, CW ;

Glorius, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15195-15201

[3] An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature [J].

Altenhoff, G ;

Goddard, R ;

Lehmann, CW ;

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3690-3693

[4] Orthogonal Pd- and Cu-based catalyst systems for C- and N-arylation of oxindoles [J].

Altman, Ryan A. ;

Hyde, Alan M. ;

Huang, Xiaohua ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9613-9620

[5] 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

[6] Heck reactions of 2-substituted enol ethers with aryl bromides catalysed by a tetraphosphine/palladium complex [J].

Battace, A ;

Zair, T ;

Doucet, H ;

Santelli, M .

TETRAHEDRON LETTERS, 2006, 47 (04) :459-462

[7] Heck reactions of α- or β-substituted enol ethers with aryl bromides catalysed by a Tetraphosphane/Palladium complex -: direct access to acetophenone or 1-arylpropanone derivatives [J].

Battace, Ahmed ;

Feuerstein, Marie ;

Lemhadri, Mhamed ;

Zair, Touriya ;

Doucet, Henri ;

Santelli, Maurice .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (19) :3122-3132

[8] Heck vinylations using vinyl sulfide, vinyl sulfoxide, vinyl sulfone, or vinyl sulfonate derivatives and aryl bromides catalyzed by a palladium complex derived from a tetraphosphine [J].

Battace, Ahmed ;

Zair, Touriya ;

Doucet, Henri ;

Santelli, Maurice .

SYNTHESIS-STUTTGART, 2006, 20 (20) :3495-3505

[9] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].

Bellina, F ;

Carpita, A ;

Rossi, R .

SYNTHESIS-STUTTGART, 2004, (15) :2419-2440

[10] Heck reactions of aryl halides with alk-1-en-3-ol derivatives catalysed by a tetraphosphine-palladium complex [J].

Berthiol, Florian ;

Doucet, Henri ;

Santelli, Maurice .

APPLIED ORGANOMETALLIC CHEMISTRY, 2006, 20 (12) :855-868

← 1 2 3 4 5 →