Synthesis and Reactivity of 2‐Arylquinazoline Halidoruthenacycles in Arylation Reactions

@article{Kuzman2017SynthesisAR,
  title={Synthesis and Reactivity of 2‐Arylquinazoline Halidoruthenacycles in Arylation Reactions},
  author={Petra Kuzman and Franc Po{\vz}gan and Anton Meden and Jurij Svete and Bogdan {\vS}tefane},
  journal={ChemCatChem},
  year={2017},
  volume={9}
}
The synthesis of a range of new cyclometallated organoruthenium(II) complexes through the ortho‐C−H activation of the aryl group in 2‐aryl‐substituted quinazolines with [RuX2(p‐cymene)]2 is described. The beneficial effect of the carboxylate ligand on both the cyclometallation and the further arylation reaction step was demonstrated. Mechanistic studies reveal that bromide and iodide anions decelerate the arylation process by an in situ ligand exchange reaction. Additionally, a detailed NMR… 
11 Citations
Microwave‐Promoted ortho‐C−H Bond (Hetero)arylation of Arylpyrimidines in Water Catalyzed by Ruthenium(II)−Carboxylate
Efficient diarylation of ortho‐C−H bonds of 2‐arylpyrimidines was achieved by Ru(II)−carboxylate‐catalyzed reaction with aryl bromides in water, whereas meta‐substituted phenylpyrimidines selectively
Insights into mechanism and selectivity in ruthenium(II)-catalysed ortho-arylation reactions directed by Lewis basic groups
We report a detailed study of the selectivity of ruthenium-catalysed C–H arylation reactions directed by Lewis basic heterocycles. A reactivity scale for directing power in these reactions, based on
Ruthenium(II)-Catalyzed Microwave-Promoted Multiple C-H Activation in Synthesis of Hexa(heteroaryl)benzenes in Water.
TLDR
A series of hexa(heteroaryl)benzenes were synthesized by the Ru(II)-carboxylate-catalyzed multiple C-H activation of benzenes carrying pyridyl, pyrimids, or pyrazolyl directing groups using N-hetero Daryl bromides as coupling partners, providing multidentate ligands for selective complexation of transition metals and potential building of photoredox systems.
Arene Ruthenium Catalyst MCAT-53 for the Synthesis of Heterobiaryl Compounds in Water through Aromatic C–H Bond Activation
A new water friendly MCAT-53 [Ru2Cl2 (HCOO)3(p-cymene)] Na (sodium η-6-p-cymene dichloro diruthenium triformato complex) has been developed as a catalyst to effect aromatic C–H bond activation and
Conformationally Driven Ru(II)-Catalyzed Multiple ortho-C–H Bond Activation in Diphenylpyrazine Derivatives in Water: Where Is the Limit?
Ru(II)/carboxylate/PPh3 catalyst system enabled the preparation of highly conjugated pyrazine derivatives in water under microwave irradiation. Both nitrogen atoms efficiently dictated cleavage of
Cyclometallated ruthenium catalyst enables late-stage directed arylation of pharmaceuticals
TLDR
A class of ruthenium catalysts that display a unique efficacy towards late-stage arylation of heavily functionalized substrates of biaryls decorated with polar and delicate functionalities are introduced.
Straightforward Access to 3,4‐Dihydro‐2H‐1,2,4‐benzothiadiazine 1,1‐dioxides and Quinazolines via Iron‐Catalyzed Aerobic Oxidative Condensation of Amines
Page 1 Title Dr First Name Gopalaiah Last Name Kovuru Photograph Designation Assistant Professor Address Room No.: 3, Block-C Department of Chemistry University of Delhi, North Campus Delhi‐110007,
...
1
2
...

References

SHOWING 1-10 OF 105 REFERENCES
Ru-Catalysed C–H Arylation of Indoles and Pyrroles with Boronic Acids: Scope and Mechanistic Studies
TLDR
The Ru-catalysed C2–H arylation of indoles and pyrroles by using boronic acids under oxidative conditions is reported and Mechanistic studies suggest the on-cycle intermediates do not possess a para-cymene ligand and that theOn-cycle metalation occurs through an electrophilic attack by the Ru centre.
C–H Bond Functionalization of Arylpyrimidines Catalyzed by an in situ Generated Ruthenium(II) Carboxylate System and the Construction of Tris(heteroaryl)‐Substituted Benzenes
A ruthenium(II) carboxylate catalyst, generated in situ from [RuCl 2 (p-cymene)] 2 and 1-phenyl-1-cyclopentanecarboxylic acid (PCCA) in the presence of K 2 CO 3 , allowed activation of the C―H bond
Ruthenium‐Catalyzed C−H Arylation of Benzoic Acids and Indole Carboxylic Acids with Aryl Halides
TLDR
The first Ru‐catalyzed C−H arylation of benzoic acids with readily available aryl (pseudo)halides with efficiently applied protocol can efficiently be applied to indole carboxylic acids, thus allowing access to C7‐, C6‐,C5‐ and C4‐arylated indole compounds.
Quinazoline‐Directed C–H Bond Functionalization Catalyzed by Ruthenium(II) Carboxylate – Construction of Polyconjugated Aryl‐Heteroaryl Systems
A series of coupling products have been prepared by a ruthenium(II)-catalyzed direct ortho-C–H arylation of 2-(aryl/heteroaryl)-substituted quinazolines with (hetero)aryl bromides.
Palladium-catalyzed ortho-arylation of benzamides via direct sp(2) C-H bond activation.
The palladium-catalyzed ortho-arylation of benzamides by aryl iodides has been demonstrated with the simplest amide CONH(2) as a directing group for the first time. This protocol can be applied to
Carbon-hydrogen bond functionalization approach for the synthesis of fluorenones and ortho-arylated benzonitriles.
A sequence consisting of palladium-catalyzed benzamide ortho-arylation/reaction with (CF3CO)2O was developed allowing a convenient one-pot synthesis of ortho-arylated benzonitriles and fluorenone
Pd-catalyzed ortho-arylation of phenylacetamides, benzamides, and anilides with simple arenes using sodium persulfate
We report a mild and efficient Pd-catalyzed ortho-arylation of phenylacetamides, benzamides, and anilides with a range of simple arenes using sodium persulfate (Na2S2O8). This green strategy
Ru-Catalyzed C–H Arylation of Fluoroarenes with Aryl Halides
TLDR
Deuterium labeling and kinetic isotope effect experiments indicate that C–H activation is both reversible and kinetically significant and Computational studies support a concerted metalation–deprotonation (CMD)-type ruthenation mode and shed light on the unusual arylation regioselectivity.
...
1
2
3
4
5
...