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

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.

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ChemInform Abstract: Synthesis of Condensed Heteroaromatic Compounds by Palladium-Catalyzed Oxidative Coupling of Heteroarene Carboxylic Acids with Alkynes.

ChemInform ◽

10.1002/chin.200945122 ◽

2009 ◽

Vol 40 (45) ◽

Author(s):

Mana Yamashita ◽

Koji Hirano ◽

Tetsuya Satoh ◽

Masahiro Miura

Keyword(s):

Carboxylic Acids ◽

Oxidative Coupling ◽

Heteroaromatic Compounds ◽

Palladium Catalyzed

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Ru(II)-Catalyzed Difunctional Pyridyloxy-Directed Regio- and Stereospecific Addition of Carboxylic Acids to Internal Alkynes

Organic Letters ◽

10.1021/acs.orglett.1c04052 ◽

2021 ◽

Author(s):

Qin Wang ◽

Yan Shi ◽

Xiaoli Huang ◽

Yongzhuang Wang ◽

Jiao Jiao ◽

...

Keyword(s):

Carboxylic Acids ◽

Internal Alkynes

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ChemInform Abstract: Indole Synthesis via Cobalt(III)-Catalyzed Oxidative Coupling of N-Arylureas and Internal Alkynes.

ChemInform ◽

10.1002/chin.201633133 ◽

2016 ◽

Vol 47 (33) ◽

Author(s):

Zhuo-Zhuo Zhang ◽

Bin Liu ◽

Jing-Wen Xu ◽

Sheng-Yi Yan ◽

Bing-Feng Shi

Keyword(s):

Oxidative Coupling ◽

Internal Alkynes ◽

Indole Synthesis

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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

The Journal of Organic Chemistry ◽

10.1021/acs.joc.8b00638 ◽

2018 ◽

Vol 83 (10) ◽

pp. 5639-5649 ◽

Cited By ~ 19

Author(s):

Takeshi Okada ◽

Asumi Sakai ◽

Tomoaki Hinoue ◽

Tetsuya Satoh ◽

Yoshihiro Hayashi ◽

...

Keyword(s):

Carboxylic Acids ◽

Oxidative Coupling ◽

Bond Cleavage

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Rhodium(iii)-catalysed carboxylate-directed C–H functionalizations of isoxazoles with alkynes

Chemical Communications ◽

10.1039/c9cc03283e ◽

2019 ◽

Vol 55 (58) ◽

pp. 8382-8385 ◽

Cited By ~ 9

Author(s):

Somaraju Yugandar ◽

Hiroyuki Nakamura

Keyword(s):

Carboxylic Acids ◽

Internal Alkynes

Isoxazolyl-4-carboxylic acids underwent rhodium(iii)-catalysed carboxylate-directed C–H functionalizations with internal alkynes to produce pyranoisoxazolones, isoquinolines, and 5-alkenylisoxazoles controlled by oxidants.

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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)

Zeitschrift für Naturforschung B ◽

10.1515/znb-1983-0709 ◽

1983 ◽

Vol 38 (7) ◽

pp. 835-840 ◽

Cited By ~ 32

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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