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

A metal-free oxidative coupling reaction of trifluoromethyl β-diketones with alcohols for the synthesis of α-keto esters in good to excellent yields has been developed. Preliminary mechanistic studies suggest that an I2/TBHP promoted sequential iodination, C–C bond cleavage, C–O bond formation and oxidation pathway is involved in this reaction.

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ChemInform Abstract: Direct Amidation of Carboxylic Acids with Tertiary Amines: Amide Formation over Copper Catalysts Through C-N Bond Cleavage.

ChemInform ◽

10.1002/chin.201508121 ◽

2015 ◽

Vol 46 (8) ◽

pp. no-no

Author(s):

Biquan Xiong ◽

Longzhi Zhu ◽

Xiaofeng Feng ◽

Jian Lei ◽

Tieqiao Chen ◽

...

Keyword(s):

Carboxylic Acids ◽

Bond Cleavage ◽

Copper Catalysts ◽

Tertiary Amines ◽

Amide Formation ◽

Direct Amidation

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

Organic & Biomolecular Chemistry ◽

10.1039/c7ob01497j ◽

2017 ◽

Vol 15 (42) ◽

pp. 8904-8913 ◽

Cited By ~ 7

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.

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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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