Ni-Catalyzed Carboxylation of Conjugated Dienes with Carbon Dioxide and DIBAL-H for the Synthesis of ß,γ-Unsaturated Carboxylic Acids

Synlett ◽  
2020 ◽  
Author(s):  
Masanari Kimura ◽  
Ying Luo ◽  
Bun Chan ◽  
Tsutomu Fukuda ◽  
Gen Onodera
Keyword(s):  
Carbon Dioxide ◽  
Carboxylic Acids ◽  
Atmospheric Pressure ◽  
Conjugated Dienes ◽  
Ni Catalyst ◽  
Diisobutylaluminum Hydride ◽  
Unsaturated Carboxylic Acids

Ni-catalyst-promoted conjugated dienes undergo 1,2-hydrocarboxylation with carbon dioxide under atmospheric pressure and in the presence of diisobutylaluminum hydride (DIBAL-H). Conjugated dienes react with carbon dioxide in a 1:1 ratio to produce the corresponding β,γ-unsaturated carboxylic acids without suffering from the dimerization or oligomerization of conjugated dienes.

scholarly journals Cp2TiCl2-catalyzed hydrocarboxylation of alkynes with CO2: formation of α,β-unsaturated carboxylic acids

RSC Advances ◽  
2017 ◽  
Vol 7 (6) ◽  
pp. 3534-3539 ◽  
Author(s):  
Peng Shao ◽  
Sheng Wang ◽  
Gaixia Du ◽  
Chanjuan Xi
Keyword(s):  
Carboxylic Acids ◽  
Atmospheric Pressure ◽  
Unsaturated Carboxylic Acids ◽  
High Yields

Cp2TiCl2-catalyzed hydrocarboxylation of alkynes with CO2 (atmospheric pressure) has been reported. A range of alkynes were transformed to the corresponding α,β-unsaturated carboxylic acids in high yields with high regioselectivity.

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.

Nickel-catalyzed electrocarboxylation of allylic halides with CO2

2021 ◽  
Author(s):  
Laxia Wu ◽  
Deng Fangjie ◽  
Lin Wu ◽  
Huan Wang ◽  
TaiJie Chen ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Current Density ◽  
Atmospheric Pressure ◽  
Reaction Parameters ◽  
Unsaturated Carboxylic Acids ◽  
Allylic Halides

Nickel-catalyzed regioselective electrocarboxylation of allylic halides with CO2 at atmospheric pressure has been developed by adjusting reaction parameters, including catalyst, solvent, current density, temperature and additive. β,γ-unsaturated carboxylic acids were...

Asymmetric hydrogenation of α,β-unsaturated carboxylic acids in supercritical carbon dioxide

1996 ◽  
Vol 37 (16) ◽  
pp. 2813-2816 ◽  
Author(s):  
Jianliang Xiao ◽  
Sylvia C.A. Nefkens ◽  
Philip G. Jessop ◽  
Takao Ikariya ◽  
Ryoji Noyori
Keyword(s):  
Carbon Dioxide ◽  
Supercritical Carbon Dioxide ◽  
Carboxylic Acids ◽  
Asymmetric Hydrogenation ◽  
Unsaturated Carboxylic Acids ◽  
Supercritical Carbon
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