An Active, General, and Long-Lived Palladium Catalyst for Cross-Couplings of Deactivated (Hetero)aryl Chlorides and Bromides with Arylboronic Acids

被引：18

作者：

Hoshi, Takashi ^{[1
]}

Honma, Tomonobu ^{[1
]}

Mori, Ayako ^{[1
]}

Konishi, Maki ^{[1
]}

Sato, Tsutomu ^{[1
]}

Hagiwara, Hisahiro ^{[1
]}

Suzuki, Toshio ^{[1
]}

机构：

[1] Niigata Univ, Dept Chem & Chem Engn, Niigata 9502181, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 22期

关键词：

BIPHENYLENE-SUBSTITUTED RUTHENOCENYLPHOSPHINE; HINDERED ARYL CHLORIDES; C-N; PHOSPHINE-LIGANDS; SUZUKI; EFFICIENT; COMPLEXES; AMINATION; PRECATALYSTS; HALIDES;

D O I：

10.1021/jo402089r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An active, general, and long-lived palladium catalyst for Suzuki-Miyaura reactions of aryl and heteroaryl chlorides deactivated by steric hindrance, electron richness, and coordinating functional groups is reported. In reactions of arylbromide bearing two o-tert-butyl substituents, C(sp(3))-H arylation of the tert-butyl group, rather than the Suzuki-Miyaura reaction, proceeded in excellent yield. The key to the success of the reactions was the development of biphenylene-substituted dicyclohexylruthenocenylphosphine (CyR-Phos) as a supporting ligand.

引用

页码：11513 / 11524

页数：12

共 75 条

[1] Efficient aryl-(hetero)aryl coupling by activation of C-Cl and C-F bonds using nickel complexes of air-stable phosphine oxides [J].

Ackermann, L ;

Born, R ;

Spatz, JH ;

Meyer, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (44) :7216-7219

[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] General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water [J].

Anderson, KW ;

Buchwald, SL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6173-6177

[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] Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters [J].

Billingsley, Kelvin ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) :3358-3366

[7] A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds [J].

Billingsley, Kelvin L. ;

Anderson, Kevin W. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (21) :3484-3488

[8] A new class of easily activated palladium precatalysts for facile C-N cross-coupling reactions and the low temperature oxidative addition of aryl chlorides [J].

Biscoe, Mark R. ;

Fors, Brett P. ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (21) :6686-+

[9] Pd-PEPPSI-IPent: Low-Temperature Negishi Cross-Coupling for the Preparation of Highly Functionalized, Tetra-ortho-Substituted Biaryls [J].

Calimsiz, Selcuk ;

Sayah, Mahmoud ;

Mallik, Debasis ;

Organ, Michael G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (11) :2014-2017

[10] An efficient and cost-effective synthesis of 2-phenyl-3-aminopyridine [J].

Caron, S ;

Massett, SS ;

Bogle, DE ;

Castaldi, MJ ;

Braish, TF .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (03) :254-256

← 1 2 3 4 5 6 7 8 →