Subtle Steric Effects in Nickel-Catalysed Kumada-Tamao-Corriu Cross-Coupling Using Resorcinarenyl-Imidazolium Salts

2013 ◽  
Vol 2013 (20) ◽  
pp. 4443-4449 ◽  
Author(s):  
Neslihan Şahin ◽  
David Sémeril ◽  
Eric Brenner ◽  
Dominique Matt ◽  
İsmail Özdemir ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Steric Effects ◽  
Imidazolium Salts

Synthesis of glucoside-based imidazolium salts for Pd-catalyzed cross-coupling reaction in water

2020 ◽  
Vol 496 ◽  
pp. 108079
Author(s):  
Zhonggao Zhou ◽  
Qian Xie ◽  
Xin Zhou ◽  
Yangyang Yuan ◽  
Yan Pan ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Imidazolium Salts ◽  
Cross Coupling Reaction ◽  
Reaction In Water

Nickel-Catalyzed Regioselective Reductive Cross-Coupling of Aryl Halides with Polysubstituted Allyl Halides in the Presence of Imidazolium Salts

Synlett ◽  
2015 ◽  
Vol 26 (20) ◽  
pp. 2784-2788 ◽  
Author(s):  
Hongjun Ren ◽  
Zhan Zhang ◽  
Lijun Xu ◽  
Zhengkai Chen ◽  
Zhubo Liu ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Aryl Halides ◽  
Imidazolium Salts ◽  
Allyl Halides

ChemInform Abstract: Cross-Coupling of Polychlorobenzenes with Phenylboronic Acid in the Presence of [Pd]-Imidazolium Salts as Catalytic Systems.

ChemInform ◽  
2008 ◽  
Vol 39 (23) ◽  
Author(s):  
A. S. Burukin ◽  
A. A. Vasil'ev ◽  
N. L. Merkulova ◽  
A. O. Chizhov ◽  
E. A. Mistryukov ◽  
...  
Keyword(s):  
Phenylboronic Acid ◽  
Cross Coupling ◽  
Imidazolium Salts ◽  
Catalytic Systems

scholarly journals N-Directed Pd-Catalyzed Photoredox-Mediated C–H Arylation for Accessing Phenyl-Extended Analogues of Biginelli/Suzuki-Derived Ethyl 4-Methyl-2,6-diphenylpyrimidine-5-carboxylates

Catalysts ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 1071
Author(s):  
Savvas N. Georgiades ◽  
Persefoni G. Nicolaou ◽  
Nikos Panagiotou
Keyword(s):  
Organic Synthesis ◽  
Phenyl Ring ◽  
Room Temperature ◽  
Functional Group ◽  
Cross Coupling ◽  
Steric Effects ◽  
Biologically Relevant ◽  
Biginelli Condensation ◽  
Derivatives Of ◽  
Electronic And Steric Effects

The availability and application of direct, functional group-compatible C–H activation methods for late-stage modification of small-molecule bioactives and other valuable materials remains an ongoing challenge in organic synthesis. In the current study, we demonstrate that a LED-activated, photoredox-mediated, Pd(OAc)2-catalyzed C–H arylation, employing a phenyldiazonium aryl source and either tris(2,2′-bipyridine)ruthenium(II) or (2,2′-bipyridine)bis[3,5-di-fluoro-2-[5-(trifluoromethyl)-2-pyridinyl-kN][phenyl-kC]iridium(III) as photoredox initiator, may successfully produce unprecedented mono- and bis-phenyl derivatives of functionality-rich 2,6-diphenylpyrimidine substrates at room temperature. The series of 19 substrates employed herein, which share the biologically-relevant 4-methyl-2,6-diphenylpyrimidine-5-carboxylate scaffold, were generated via a synthetic route involving (3-component) Biginelli condensation, oxidative dehydrogenation of the obtained 3,4-dihydropyrimidin-2(1H)-one to 2-hydroxypyrimidine, O-sulfonylation, and Suzuki-Miyaura C–C cross-coupling. Submission of these substrates to pyrimidine-N-atom-directed C–H arylation conditions led to regioselective phenylation at the ortho site(s) of the pyrimidine-C2-connected phenyl ring, revealing substituent-dependent electronic and steric effects. A focused library of 18 mono- and 10 bis-phenyl derivatives was generated. Its members exhibit interesting 3D and peripheral substitution features that render them promising for evaluation in drug discovery efforts.

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