Ultrasound promoted Suzuki cross-coupling reactions in ionic liquid at ambient conditions

2002 ◽  
pp. 616-617 ◽  
Author(s):  
R. Rajagopal ◽  
Dilip V. Jarikote ◽  
K. V. Srinivasan
Keyword(s):  
Ionic Liquid ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Ambient Conditions ◽  
Cross Coupling Reactions

Palladium Nanoparticles Stabilized by an Ionic Polymer and Ionic Liquid: A Versatile System for C−C Cross-Coupling Reactions

2008 ◽  
Vol 47 (8) ◽  
pp. 3292-3297 ◽  
Author(s):  
Xue Yang ◽  
Zhaofu Fei ◽  
Dongbin Zhao ◽  
Wee Han Ang ◽  
Yongdan Li ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Palladium Nanoparticles ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Ionic Polymer ◽  
Cross Coupling Reactions

ChemInform Abstract: A New Recyclable/Reusable Ionic Liquid/LiCl System for Suzuki-Miyaura Cross Coupling Reactions.

ChemInform ◽  
2014 ◽  
Vol 45 (38) ◽  
pp. no-no
Author(s):  
Preeti Rekha Boruah ◽  
Milon J. Koiri ◽  
Utpal Bora ◽  
Diganta Sarma
Keyword(s):  
Ionic Liquid ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Ionic liquid supported tin reagents for Stille cross coupling reactions

2007 ◽  
Vol 9 (5) ◽  
pp. 431 ◽  
Author(s):  
J?rgen Vitz ◽  
Dinh Hung Mac ◽  
St?phanie Legoupy
Keyword(s):  
Ionic Liquid ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

scholarly journals Ni-Catalyzed Electrochemical C(sp2)−C(sp3) Cross-Coupling Reactions

2020 ◽  
Author(s):  
Jian Luo ◽  
Bo Hu ◽  
wenda wu ◽  
maowei hu ◽  
Tianbiao Liu
Keyword(s):  
Aryl Halide ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Ambient Conditions ◽  
Acid Modification ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Organozinc Reagents ◽  
Industrial Adoption

Nickel (Ni) catalyzed carbon-carbon (C−C) cross-coupling has been considerably developed in last decades and has demonstrated unique reactivities compared to palladium. However, existing Ni catalyzed cross-coupling reactions, despite success in organic synthesis, are still subject to the use of air-sensitive nucleophiles (i.e. Grignard and organozinc reagents), or catalysts (i.e. Ni<sup>0</sup> pre-catalysts), significantly limiting their academic and industrial adoption. Herein, we report that, through electrochemical voltammetry screening and optimization, the redox neutral C(sp<sup>2</sup>)‒C(sp<sup>3</sup>) cross-coupling can be accomplished in an undivided cell configuration using bench-stable aryl halide or β-bromostyrene (electrophiles) and benzylic trifluoroborate (nucleophiles) reactants, non-precious, bench stable catalysts consisting of NiCl<sub>2</sub>•glyme pre-catalyst and polypyridine ligands under ambient conditions. The broad reaction scope and good yields of the Ni-catalyzed electrochemical coupling reaction were confirmed by 48 examples of aryl/β-styrenyl chloride/bromide and benzylic trifluoroborates. Its potential applications were demonstrated by late-stage functionalization of pharmaceuticals and natural amino acid modification. Furthermore, this electrochemical C−C cross-coupling reaction was demonstrated at gram-scale in a flow-cell electrolyzer for practical industrial adoption. Finally, an array of chemical and electrochemical studies mechanistically indicates that electrochemical C−C cross-coupling reaction proceeds through an unconventional radical trans-metalation mechanism.

Ionic liquids in cross-coupling reactions: “liquid” solutions to a “solid” precipitation problem

2018 ◽  
Vol 54 (16) ◽  
pp. 2056-2059 ◽  
Author(s):  
Hemant Choudhary ◽  
Paula Berton ◽  
Gabriela Gurau ◽  
Allan S. Myerson ◽  
Robin D. Rogers
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Salt Precipitation ◽  
Solid Precipitation ◽  
Cross Coupling Reactions ◽  
Solid Salt ◽  
Liquid Solutions

To alleviate the problem of solid salt precipitation when using inorganic bases in cross-coupling reactions, basic anions were combined with the trihexyl(tetradecyl)phosphonium ([P66614]+) cation to ensure an ionic liquid byproduct.

Cross-coupling reactions in water using ionic liquid-based palladium(II)-phosphinite complexes as outstanding catalysts

2014 ◽  
Vol 28 (11) ◽  
pp. 818-825 ◽  
Author(s):  
Nermin Meriç ◽  
Murat Aydemir ◽  
Uğur Işik ◽  
Yusuf Selim Ocak ◽  
Khadichakhan Rafikova ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

scholarly journals Ni-Catalyzed Electrochemical C(sp2)−C(sp3) Cross-Coupling Reactions

2020 ◽  
Author(s):  
Jian Luo ◽  
Bo Hu ◽  
wenda wu ◽  
maowei hu ◽  
Tianbiao Liu
Keyword(s):  
Aryl Halide ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Ambient Conditions ◽  
Acid Modification ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Organozinc Reagents ◽  
Industrial Adoption

Nickel (Ni) catalyzed carbon-carbon (C−C) cross-coupling has been considerably developed in last decades and has demonstrated unique reactivities compared to palladium. However, existing Ni catalyzed cross-coupling reactions, despite success in organic synthesis, are still subject to the use of air-sensitive nucleophiles (i.e. Grignard and organozinc reagents), or catalysts (i.e. Ni<sup>0</sup> pre-catalysts), significantly limiting their academic and industrial adoption. Herein, we report that, through electrochemical voltammetry screening and optimization, the redox neutral C(sp<sup>2</sup>)‒C(sp<sup>3</sup>) cross-coupling can be accomplished in an undivided cell configuration using bench-stable aryl halide or β-bromostyrene (electrophiles) and benzylic trifluoroborate (nucleophiles) reactants, non-precious, bench stable catalysts consisting of NiCl<sub>2</sub>•glyme pre-catalyst and polypyridine ligands under ambient conditions. The broad reaction scope and good yields of the Ni-catalyzed electrochemical coupling reaction were confirmed by 48 examples of aryl/β-styrenyl chloride/bromide and benzylic trifluoroborates. Its potential applications were demonstrated by late-stage functionalization of pharmaceuticals and natural amino acid modification. Furthermore, this electrochemical C−C cross-coupling reaction was demonstrated at gram-scale in a flow-cell electrolyzer for practical industrial adoption. Finally, an array of chemical and electrochemical studies mechanistically indicates that electrochemical C−C cross-coupling reaction proceeds through an unconventional radical trans-metalation mechanism.

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