The Highly Efficient Suzuki-Miyaura Cross-Coupling of (Hetero)aryl Chlorides and (Hetero)arylboronic Acids Catalyzed by "Bulky-yet-Flexible" Palladium-PEPPSI Complexes in Air

被引：52

作者：

Ouyang, Jia-Sheng ^{[1
]}

Li, Yan-Fang ^{[1
]}

Huang, Fei-Dong ^{[1
]}

Lu, Dong-Dong ^{[1
]}

Liu, Feng-Shou ^{[1
]}

机构：

[1] Guangdong Pharmaceut Univ, Guangdong Cosmet Engn & Technol Res Ctr, Sch Chem & Chem Engn, Zhongshan 528458, Guangdong, Peoples R China

来源：

CHEMCATCHEM | 2018年 / 10卷 / 02期

关键词：

biaryls; boron; carbenes; cross-coupling; palladium; N-HETEROCYCLIC CARBENE; ORTHO-SUBSTITUTED BIARYLS; BUCHWALD-HARTWIG AMINATION; ROOM-TEMPERATURE; ARYL CHLORIDES; HETEROARYL HALIDES; AEROBIC CONDITIONS; GENERAL-METHOD; BORONIC ACIDS; PRE-CATALYST;

D O I：

10.1002/cctc.201701076

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A series of Pd-PEPPSI complexes were designed and synthesized. The relationship between catalyst structure and properties was systematically investigated. It was revealed that bulky-yet-flexible C3 bearing ancenaphthyl backbone was a highly efficient precatalyst and could be successfully employed in Suzuki-Miyaura reactions of (hetero)aryl chlorides with (hetero)arylboronic acids at a low palladium loading in the presence of a weak inorganic base in air.

引用

页码：371 / 375

页数：5

共 54 条

[1] Development of Structurally Diverse N-Heterocyclic Carbene Ligands via Palladium-Copper-Catalyzed Decarboxylative Arylation of Pyrazolo[1,5-a]pyridine-3-carboxylic Acid [J].

Alam, Khyarul ;

Kim, Seong Min ;

Kim, Do Joong ;

Park, Jin Kyoon .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (16) :2661-2670

[2] Site-selective Suzuki-Miyaura coupling of heteroaryl halides - understanding the trends for pharmaceutically important classes [J].

Almond-Thynne, Joshua ;

Blakemore, David C. ;

Pryde, David C. ;

Spivey, Alan C. .

CHEMICAL SCIENCE, 2017, 8 (01) :40-62

[3] 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

[4]

[Anonymous], 2012, ANGEW

[5] Palladium N-Heterocyclic Carbene Catalysts for the Ultrasound-Promoted Suzuki-Miyaura Reaction in Glycerol [J].

Azua, Arturo ;

Mata, Jose A. ;

Heymes, Pauline ;

Peris, Eduardo ;

Lamaty, Frederic ;

Martinez, Jean ;

Colacino, Evelina .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (06) :1107-1116

[6] Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Esters [J].

Ben Halima, Taoufik ;

Zhang, Wanying ;

Yalaoui, Imane ;

Hong, Xin ;

Yang, Yun-Fang ;

Houk, Kendall N. ;

Newman, Stephen G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (03) :1311-1318

[7] An Efficient Palladium-NHC (NHC=N-Heterocyclic Carbene) and Aryl Amination Pre-Catalyst: [Pd(IPr*)(cinnamyl)Cl] [J].

Chartoire, Anthony ;

Frogneux, Xavier ;

Nolan, Steven P. .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (10) :1897-1901

[8] [Pd(IPr*)(cinnamyl)Cl]: An Efficient Pre-catalyst for the Preparation of Tetra-ortho-substituted Biaryls by Suzuki-Miyaura Cross-Coupling [J].

Chartoire, Anthony ;

Lesieur, Mathieu ;

Falivene, Laura ;

Slawin, Alexandra M. Z. ;

Cavallo, Luigi ;

Cazin, Catherine S. J. ;

Nolan, Steven P. .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (15) :4517-4521

[9] Tri(1-adamantyl)phosphine: Expanding the Boundary of Electron-Releasing Character Available to Organophosphorus Compounds [J].

Chen, Liye ;

Ren, Peng ;

Carrow, Brad P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (20) :6392-6395

[10] Remote Substitution on N-Heterocyclic Carbenes Heightens the Catalytic Reactivity of Their Palladium Complexes [J].

Dible, Benjamin R. ;

Cowley, Ryan E. ;

Holland, Patrick L. .

ORGANOMETALLICS, 2011, 30 (19) :5123-5132

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