Recent Advances in Pd-Catalyzed Cross-Coupling Reaction in Ionic Liquids

被引：102

作者：

Li, Jianxiao ^{[1
]}

Yang, Shaorong ^{[1
]}

Wu, Wanqing ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] South China Univ Technol, Key Lab Funct Mol Engn Guangdong Prov, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 11期

基金：

中国国家自然科学基金;

关键词：

Palladium; Cross-coupling; Ionic liquids; Synthetic methods; Reaction mechanisms; Green solvents; N-HETEROCYCLIC CARBENE; SUPERCRITICAL CARBON-DIOXIDE; ARYL BORONIC ACIDS; GAMMA-LACTONES; STEREOSELECTIVE-SYNTHESIS; ORGANIC-SYNTHESIS; TERMINAL ALKYNES; AQUEOUS-MEDIA; PALLADIUM NANOPARTICLES; SONOGASHIRA REACTIONS;

D O I：

10.1002/ejoc.201701509

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ionic liquids (ILs) can behave as green solvents in comparison with conventional organic solvents, but more often they also act as ligands, co-catalysts, and stabilizing agents both for metal active species and for intermediates of catalytic systems. In this review we have mainly summarized the recent achievements (2013 to the present) in Pd-catalyzed cross-coupling in ILs for the assembly of structurally diverse and highly functionalized organic molecules, with the focus on cascade reactions triggered by nucleopalladation, Suzuki coupling, Sonogashira coupling, allylic functionalization, and other types of coupling. The reaction conditions, regio- and stereoselectivities, and mechanisms are summarized in detail. We also highlight important and representative examples and synthetic applications of these coupling reactions. We hope that this review will result in further focused research to widen the comprehension and application of ILs in the future.

引用

页码：1284 / 1306

页数：23

共 163 条

[1] Bromopalladation Triggering the Cascade Oxidative Heterocyclization Reaction of Alkynes with Alkenes in Ionic Liquids [J].

An, Yanni ;

Li, Jianxiao ;

Zhang, Zhenming ;

Li, Chunsheng ;

Yang, Shaorong .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (09) :2136-2141

[2] Parallel developments in aprotic and protic ionic liquids: Physical chemistry and applications [J].

Angell, C. Austen ;

Byrne, Nolene ;

Belieres, Jean-Philippe .

ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (11) :1228-1236

[3]

[Anonymous], 2014, ANGEW CHE, DOI DOI 10.1039/C4GC00542B

[4] Palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes.: An approach to 2-substituted 3-alkynylindoles and 2-substituted 3-acylindoles [J].

Arcadi, A ;

Cacchi, S ;

Fabrizi, G ;

Marinelli, F ;

Parisi, LM .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6213-6217

[5]

Armand M, 2009, NAT MATER, V8, P621, DOI [10.1038/nmat2448, 10.1038/NMAT2448]

[6] Supercritical and near-critical CO2 in green chemical synthesis and processing [J].

Beckman, EJ .

JOURNAL OF SUPERCRITICAL FLUIDS, 2004, 28 (2-3) :121-191

[7]

Brand J. P., 2009, ANGEW CHEM, V121, P9510

[8] Direct Alkynylation of Indole and Pyrrole Heterocycles [J].

Brand, Jonathan P. ;

Charpentier, Julie ;

Waser, Jerome .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9346-9349

[9] Efficient Palladium Catalysts Containing Original Imidazolium-Tagged Chiral Diamidophosphite Ligands for Asymmetric Allylic Substitutions in Neat Ionic Liquid [J].

Bravo, Maritza J. ;

Favier, Isabelle ;

Saffon, Nathalie ;

Ceder, Rosa M. ;

Muller, Guillermo ;

Gomez, Montserrat ;

Rocamora, Merce .

ORGANOMETALLICS, 2014, 33 (03) :771-779

[10] Non-haloaluminate room-temperature ionic liquids in electrochemistry - A review [J].

Buzzeo, MC ;

Evans, RG ;

Compton, RG .

CHEMPHYSCHEM, 2004, 5 (08) :1106-1120

← 1 2 3 4 5 6 7 8 9 10 →