NiCl2(PCy3)2:  A Simple and Efficient Catalyst Precursor for the Suzuki Cross-Coupling of Aryl Tosylates and Arylboronic Acids

Zim, Danilo; Lando, Vanusa Regina; Dupont, Jaı̈rton; Monteiro, Adriano L.

doi:10.1021/ol016526l

Cited by 298 publications

(124 citation statements)

References 17 publications

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“…The Hammett s À parameter [76,77] is an excellent descriptor in this case. Note, however, that the literature contains diverse reports: Similar correlations were reported for Suzuki, [78][79][80] Heck, [81][82][83][84][85] and carbonylation reactions [86] even though different Hammett parameters were used: Milstein and Herrmann reported that s À p parameters yielded the best fits, whereas other studies applied s p parameters. Even a s þ p correlation to establish a stabilization of a positive charge in the transition state was reported.…”

mentioning

confidence: 61%

Insights into Sonogashira Cross‐Coupling by High‐Throughput Kinetics and Descriptor Modeling

Heiden

Plenio

Immel

et al. 2008

Chemistry A European J

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A method is presented for the high-throughput monitoring of reaction kinetics in homogeneous catalysis, running up to 25 coupling reactions in a single reaction vessel. This method is demonstrated and validated on the Sonogashira reaction, analyzing the kinetics for almost 500 coupling reactions. First, one-pot reactions of phenylacetylene with a set of 20 different meta- and para-substituted aryl bromides were analyzed in the presence of 17 different Pd-phosphine complexes. In addition, the temperature-dependent Sonogashira reactions were examined for 21 different ArX (X=Cl, Br, I) substrates, and the corresponding activation enthalpies and entropies were determined by means of Eyring plots: ArI (DeltaH(not equal)=48-62 kJ mol(-1); DeltaS(not equal)=-71--39 J mol(-1) K; NO(2)-->OMe), ArBr (DeltaH(not equal)=54-82 kJ mol(-1), DeltaS(not equal)=-55-11 J mol(-1) K), and ArCl (DeltaH(not equal)=95-144 kJ mol(-1), DeltaS(not equal)=-6-100 J mol(-1) K). DFT calculations established a linear correlation of DeltaH( not equal) and the Kohn-Sham HOMO energies of ArX (X=Cl, Br, I) and confirmed their involvement in the rate-limiting step. However, despite different C--X bond energies, aryl iodides and electron-deficient aryl bromides showed similar activation parameters.

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mentioning

confidence: 61%

Insights into Sonogashira Cross‐Coupling by High‐Throughput Kinetics and Descriptor Modeling

Heiden

Plenio

Immel

et al. 2008

Chemistry A European J

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“…70 This reaction was, however, restricted to mesylates and tosylates containing EWGs. Recently, Monteiro and co-workers 71 have reported the use of the NiCl 2 (PCy 3 ) 2 catalyst in the SM cross-coupling reaction of a variety of aryl tosylates with arylboronic acid under mild reaction conditions (Scheme 28).…”

Section: Sm Cross-coupling Reactions With Other Novel Palladium Catalmentioning

confidence: 99%

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,659

530

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“…45 Nickel carboxyl cellulose (NiCC) was also evaluated for the Suzuki coupling reactions. 46 First, a test was performed for 6 h in the absence of ligands; however, no coupling product was formed. Based on this preliminary result for this reaction, it was performed again for a longer time, according to the literature, in the presence of triphenylphosphine.…”

Section: Pd-cc and Ni-cc Cross Coupling Reactionsmentioning

confidence: 99%

Cellulose Oxidation and the Use of Carboxyl Cellulose Metal Complexes in Heterogeneous Catalytic Systems to Promote Suzuki-Miyaura Coupling and C−O Bond Formation Reaction

Martins

Santos

Rodrigues

et al. 2017

J. Braz. Chem. Soc.

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This work shows the modification of microcrystalline cellulose by the selective oxidation of primary hydroxyl groups to carboxylate groups by a 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO)-mediated system and its application as a heterogeneous ligand by ionic exchange with catalytic metals ions such as palladium, nickel and copper. Afterwards is described the application of the synthesized material as catalyst in coupling reactions such as Suzuki-Miyaura coupling and C−O bond formation reaction in different conditions, which are of great importance for the synthesis of drugs, natural products and new materials such as dendrimers, liquid crystals and polymers with magnetic and optical properties. The carboxyl cellulose matrix shows to have superior catalytic results as a ligand for all coupling reactions. Can be also highlighted the affinity of the carboxyl cellulose ligand in polar solvents such as water and alcohols and its application in mild conditions.

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NiCl₂(PCy₃)₂: A Simple and Efficient Catalyst Precursor for the Suzuki Cross-Coupling of Aryl Tosylates and Arylboronic Acids

Cited by 298 publications

References 17 publications

Insights into Sonogashira Cross‐Coupling by High‐Throughput Kinetics and Descriptor Modeling

Insights into Sonogashira Cross‐Coupling by High‐Throughput Kinetics and Descriptor Modeling

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Cellulose Oxidation and the Use of Carboxyl Cellulose Metal Complexes in Heterogeneous Catalytic Systems to Promote Suzuki-Miyaura Coupling and C−O Bond Formation Reaction

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