Palladium-catalyzed oxidative carbonylation of hydrazides: synthesis of 1,3,4-oxadiazol-2(3H)-ones

2015 ◽  
Vol 51 (10) ◽  
pp. 1905-1907 ◽  
Author(s):  
Yu Wang ◽  
Xu Meng ◽  
Yuting Yang ◽  
Lutao Zhang ◽  
Shuaibo Guo ◽  
...  
Keyword(s):  
Carbon Monoxide ◽  
Carbonyl Group ◽  
Intramolecular Cyclization ◽  
Oxidative Carbonylation ◽  
Amine Group ◽  
Mild Conditions ◽  
Carbonylation Reaction ◽  
Efficient Access ◽  
Wide Range ◽  
Palladium Catalyzed

A novel palladium-catalyzed oxidative carbonylation reaction was developed via the carbon monoxide insertions between the amine group and the carbonyl group to realize the intramolecular cyclization, which provides efficient access to 1,3,4-oxadiazol-2(3H)-ones with a wide range of substrates under mild conditions, resulting in good to excellent yields.

Palladium-catalyzed carbonylation of 1,5-cyclooctadiene. Effects of temperature and pressure

1991 ◽  
Vol 56 (3) ◽  
pp. 663-672 ◽  
Author(s):  
Curtis B. Anderson ◽  
Rade Marković
Keyword(s):  
Carbon Monoxide ◽  
Oxidative Carbonylation ◽  
Influence Of Temperature ◽  
Carbonylation Reaction ◽  
Palladium Catalyzed ◽  
Effects Of Temperature ◽  
Temperature And Pressure

The influence of temperature and carbon monoxide pressure on the course of oxidative carbonylation reaction of 1,5-cyclooctadiene in the presence of the palladium(II) salts as a catalyst, was investigated.

Palladium-Catalyzed Cyanation under Mild Conditions: A Case Study to Discover Appropriate Substrates among Halides and Pseudohalides

Synlett ◽  
2020 ◽  
Vol 31 (16) ◽  
pp. 1629-1633
Author(s):  
K. Sunil ◽  
Merla Arjuna Rajendra ◽  
Ayyiliath Meleveetil Sajith ◽  
Muthipeedika Nibin Joy ◽  
Vasiliy A. Bakulev ◽  
...  
Keyword(s):  
Environmentally Benign ◽  
Potassium Hexacyanoferrate ◽  
Mild Conditions ◽  
Suitable Substrate ◽  
Wide Range ◽  
Palladium Catalyzed

A case study has been effectively carried out to identify a suitable substrate among halides and pseudohalides for the palladium-catalyzed cyanation reactions under mild conditions. Among the various substrates considered for evaluation, aryl pentafluorobenzenesulfonates and nonaflates were identified to be the best substrates when compared to corresponding halides and pseudohalides. The substoichiometric use of nontoxic, environmentally benign potassium hexacyanoferrate as a cyanide source and exceptionally milder conditions further highlights the significance of the protocol developed. A wide range of electronically biased and sterically challenging substrates provided the corresponding the nitriles in good to excellent yields.

scholarly journals Catalyst Initiation in the Oscillatory Carbonylation Reaction

2011 ◽  
Vol 2011 ◽  
pp. 1-11 ◽  
Author(s):  
Katarina Novakovic ◽  
Julie Parker
Keyword(s):  
Carbon Monoxide ◽  
Chemical Reactions ◽  
Potassium Iodide ◽  
Significant Role ◽  
Reaction Network ◽  
Oxidative Carbonylation ◽  
Heat Of Reaction ◽  
Oscillatory Reaction ◽  
Oscillatory Behaviour ◽  
Carbonylation Reaction

Palladium(II) iodide is used as a catalyst in the phenylacetylene oxidative carbonylation reaction that has demonstrated oscillatory behaviour in both pH and heat of reaction. In an attempt to extract the reaction network responsible for the oscillatory nature of this reaction, the system was divided into smaller parts and they were studied. This paper focuses on understanding the reaction network responsible for the initial reactions of palladium(II) iodide within this oscillatory reaction. The species researched include methanol, palladium(II) iodide, potassium iodide, and carbon monoxide. Several chemical reactions were considered and applied in a modelling study. The study revealed the significant role played by traces of water contained in the standard HPLC grade methanol used.

scholarly journals Palladium-Catalyzed Cross-Coupling of Gem-Bromofluoroalkenes with Alkylboronic Acids for the Synthesis of Alkylated Monofluoroalkenes

Molecules ◽  
2020 ◽  
Vol 25 (23) ◽  
pp. 5532
Author(s):  
Laëtitia Chausset-Boissarie ◽  
Nicolas Cheval ◽  
Christian Rolando
Keyword(s):  
Organic Synthesis ◽  
Functional Group ◽  
Materials Science ◽  
Cross Coupling ◽  
High Yield ◽  
Efficient Synthesis ◽  
Mild Conditions ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Novel Strategy

Monofluoroalkenes are versatile fluorinated synthons in organic synthesis, medicinal chemistry and materials science. In light of the importance of alkyl-substituted monofluoroalkenes efficient synthesis of these moieties still represents a synthetic challenge. Herein, we described a mild and efficient methodology to obtain monofluoroalkenes through a stereospecific palladium-catalyzed alkylation of gem-bromofluoroalkenes with primary and strained secondary alkylboronic acids under mild conditions. This novel strategy gives access to a wide range of functionalized tri- and tetrasubstituted monofluoroalkenes in high yield, with good functional group tolerance, independently from the gem-bromofluoroalkenes geometry.

Novel Ring Closure Carbonylation Reaction of 1,5-Cyclooctadiene in the Presence of Pd(II)-Catalysts

1992 ◽  
Vol 57 (11) ◽  
pp. 2374-2382 ◽  
Author(s):  
Curtis B. Anderson ◽  
Rade Marković
Keyword(s):  
Carbon Monoxide ◽  
Double Bond ◽  
Methylene Chloride ◽  
Ring Closure ◽  
Oxidative Carbonylation ◽  
Experimental Conditions ◽  
Carbonylation Reaction ◽  
Methanol Mixture

Oxidative carbonylation of 1,5-cyclooctadiene in methylene chloride-methanol mixture, catalyzed by Pd(II)-salts, gave rise to a bicyclic, bifunctional product under mild experimental conditions. The mechanism, involving multiple carbon monoxide and double bond insertions into the Pd(II)-carbon σ-bond, has been proposed, as being consistent with the outcome of this novel ring closure reaction.

Palladium-catalyzed aerobic oxidative carbonylation of alkynes with amines: a general access to substituted maleimides

2018 ◽  
Vol 54 (76) ◽  
pp. 10710-10713 ◽  
Author(s):  
Ji Yang ◽  
Jiawang Liu ◽  
Ralf Jackstell ◽  
Matthias Beller
Keyword(s):  
Oxidative Carbonylation ◽  
Carbonylation Reaction ◽  
Palladium Catalyzed

A catalytic oxidative carbonylation reaction was developed for the synthesis of polysubstituted maleimides from alkynes and amines with air as a green oxidant.

Iodide-Catalyzed Carbonylation–Benzylation of Benzyl Chlorides with Potassium Aryltrifluoroborates under Ambient Pressure of Carbon Monoxide

Synlett ◽  
2017 ◽  
Vol 29 (03) ◽  
pp. 369-374 ◽  
Author(s):  
Wei Han ◽  
Junjie Chen ◽  
Fengli Jin ◽  
Xiaorong Yuan
Keyword(s):  
Carbon Monoxide ◽  
Ambient Pressure ◽  
The Novel ◽  
Metal Free ◽  
Benzyl Chlorides ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Novel Method ◽  
High Yields ◽  
Co Gas

Tetra-N-butylammonium iodide (TBAI) catalyzed carbonylation–benzylation of unactivated benzyl chlorides with potassium aryltrifluoroborates using CO gas has been developed. This reaction is transition-metal free, is carried out under ambient pressure, and provides a wide range of 1,2,3-triarylpropan-1-one derivatives in high yields. The novel method represents a significant improvement over the traditional palladium-catalyzed carbonylation.

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