Waste-Free Synthesis of Condensed Heterocyclic Compounds by Rhodium-Catalyzed Oxidative Coupling of Substituted Arene or Heteroarene Carboxylic Acids with Alkynes

2009 ◽  
Vol 74 (9) ◽  
pp. 3478-3483 ◽  
Author(s):  
Masaki Shimizu ◽  
Koji Hirano ◽  
Tetsuya Satoh ◽  
Masahiro Miura
Keyword(s):  
Carboxylic Acids ◽  
Oxidative Coupling ◽  
Heterocyclic Compounds

Ru-Catalysed synthesis of fused heterocycle-pyridinones and -pyrones

2017 ◽  
Vol 15 (42) ◽  
pp. 8904-8913 ◽  
Author(s):  
S. Ruiz ◽  
C. Carrera ◽  
P. Villuendas ◽  
E. P. Urriolabeitia
Keyword(s):  
Carboxylic Acids ◽  
Oxidative Coupling ◽  
Internal Alkynes

Heterocycle-pyridinones and heterocycle-pyranones have been prepared by Ru-catalysed oxidative coupling of N-unprotected primary heterocycle-amides and heterocycle-carboxylic acids with internal alkynes.

Rhodium(III)-Catalyzed Oxidative Coupling of N-Phenylindole-3-carboxylic Acids with Alkenes and Alkynes via C4–H and C2–H/C2′–H Bond Cleavage

2018 ◽  
Vol 83 (10) ◽  
pp. 5639-5649 ◽  
Author(s):  
Takeshi Okada ◽  
Asumi Sakai ◽  
Tomoaki Hinoue ◽  
Tetsuya Satoh ◽  
Yoshihiro Hayashi ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Oxidative Coupling ◽  
Bond Cleavage

Aktivierung von CO2 an Übergangsmetallzentren: Struktur und Reaktivität eines C-C-Kopplungsproduktes von CO2 und 2.3-Dimethylbutadien am elektronenreichen Nickel(O) / Activation of CO2 at Transition Metal Centers: Structure and Reactivity of a C-C-Coupling Product of CO2 and 2,3-Dimethylbutadiene at Electron-Rich Nickel(O)

1983 ◽  
Vol 38 (7) ◽  
pp. 835-840 ◽  
Author(s):  
Dirk Walther ◽  
Eckhard Dinjus ◽  
Joachim Sieler ◽  
Nguyen Ngoc Thanh ◽  
Wolfgang Schade ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Transition Metal ◽  
Carboxylic Acids ◽  
Coordination Sphere ◽  
Oxidative Coupling ◽  
Central Atom ◽  
Carboxylate Group ◽  
Metal Centers ◽  
X Ray ◽  
Unsaturated Carboxylic Acids

Carbon dioxide reacts with 2,3-dimethylbutadiene and bis-cyclooctadiene(1,5)-nickel(O) in the presence of N,N′-tetramethyl-ethylendiamine (tmeda) to form [(3,4,5-η3)-3,4-dimethyl-3-pentenylato](N,N′-tetramethyl-ethylendiamine)-nickel(II) as the product of the oxidative coupling of CO2 and the diene. The deep red complex crystallizes in the rhombic space group Pbca. The structure was determined by an X-ray analysis. The monodendate carboxylate group, the π-allyl system and a N-atom of tmeda form a planar coordination sphere around the central atom. The distance between Ni and the second N-atom of tmeda is very long (2.314 Å). Reaction of the complex with R−X (R: H, CH3) yield 3-unsaturated carboxylic acids; tmeda can be substituted by 2,2′-bipyridine.

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