scholarly journals Scope and Mechanistic Study of the Coupling Reaction of α,β-Unsaturated Carbonyl Compounds with Alkenes: Uncovering Electronic Effects on Alkene Insertion vs Oxidative Coupling Pathways

2011 ◽  
Vol 31 (1) ◽  
pp. 495-504 ◽  
Author(s):  
Ki-Hyeok Kwon ◽  
Do W. Lee ◽  
Chae S. Yi
Keyword(s):  
Oxidative Coupling ◽  
Carbonyl Compounds ◽  
Coupling Reaction ◽  
Mechanistic Study ◽  
Electronic Effects

The oxidative coupling between benzaldehyde derivatives and phenylacetylene catalyzed by rhodium complexes via C-H bond activation

2020 ◽  
Vol 26 (1) ◽  
pp. 20-25
Author(s):  
Xinyi Zhao ◽  
Hongge Jia ◽  
Qingji Wang ◽  
Heming Song ◽  
Yanan Tang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Oxidative Coupling ◽  
Bond Activation ◽  
Coupling Reaction ◽  
Reaction Yield ◽  
Rhodium Complexes ◽  
Electronic Effects ◽  
Oxidative Coupling Reaction ◽  
Excellent Activity ◽  
Benzaldehyde Derivatives

AbstractThis paper reports the use of rhodium (Rh) catalysts for the oxidative coupling reaction between phenylacetylene and benzaldehyde derivatives via C-H bond activation. These reactions were catalyzed by Rh(l-amino acid)(cod) (the l-amino acid is l-phenylalanine, l-valine or l-proline; cod is 1,5-cyclooctadiene) to obtain chromones in 12.7–88.3% yield. These new Rh catalysts have excellent activity for the coupling reaction between phenylacetylene and different benzaldehyde derivatives. It was found that the electronic effects of the benzaldehyde derivative substituent affected the reaction yield, which is in accordance with the proposed mechanism.

An Unprecedented Cyano-Induced Sodium Nitrite-Catalyzed C(sp3)-H and C(sp2)-H Coupling Reaction

2018 ◽  
Vol 15 (7) ◽  
pp. 989-994 ◽  
Author(s):  
Ling Li ◽  
Bo Su ◽  
Yuxiu Liu ◽  
Qingmin Wang
Keyword(s):  
Sodium Nitrite ◽  
Oxidative Coupling ◽  
High Resolution Mass Spectrometry ◽  
Coupling Reaction ◽  
13C Nmr Spectroscopy ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
1H And 13C Nmr ◽  
Oxidative Coupling Reaction ◽  
Oxidative Coupling Reactions

Aim and Objective: During the investigation of sodium nitrite-catalyzed oxidative coupling reaction of aryls, an unprecedented C(sp2)-H and C(sp3)-H coupling of substituted 2-aryl acetonitrile was found. Materials and Methods: The structure of the coupled product was confirmed by 1H and 13C NMR spectroscopy and high-resolution mass spectrometry (HRMS), and comparison of its derivatives with known compounds. The effects of methoxy group in the benzene ring on the reaction were evaluated. Results: The optimized reaction conditions are summarized as follows: CF3SO3H/substrate = 1.5 equiv., NaNO2/substrate = 0.3 equiv., CH3CN as solvent. 2-(4-Methoxyphenyl)acetonitrile and 2-(3,4,5- trimethoxyphenyl)acetonitrile could also generate C(sp2)-H and C(sp3)-H coupling. The coupling reaction occurred as a typical radial mechanism. Conclusion: An unprecedented cyano-induced, NaNO2-catalyzed oxidative C(sp3)-H and C(sp2)-H coupling was reported. The reaction proceeded under very mild conditions, using O2 in the air as terminal oxidant. The unique oxidative manner might provide more inspiration for the development of intriguing oxidative coupling reactions.

A Three Component Iodine-Catalyzed Oxidative Coupling Reaction: A Heterodifunction of 3-Methylindole

2021 ◽  
Author(s):  
Wei Zhang ◽  
Shiqun Xiang ◽  
Weibin Fan ◽  
Jiang Jin ◽  
Yinghua Li ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Peroxy Radicals ◽  
Metal Free ◽  
Tert Butyl ◽  
Oxidative Coupling Reaction

A metal-free synthesis of heterodifunctional indole derivaties is developed through TBHP/KI-mediated oxidative coupling. The reaction constructs C-O and C-C bonds in succession with the help of tert-butyl peroxy radicals generated...

Direct visualization of photo-induced disulfides through oxidative coupling of para-aminothiophenol

2021 ◽  
Author(s):  
Wei He ◽  
Chang Xia ◽  
Peng Fei Gao ◽  
Jun Zhou ◽  
Yuan Fang Li ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Chemical Transformations ◽  
Direct Visualization ◽  
Oxidative Coupling Reaction ◽  
Visible Irradiation

Chemical transformations under visible irradiation are interesting in green preparation. Herein, photo-oxidative coupling reaction of para-aminothiophenol(p-ATP) dimerizing to 4-aminophenyl disulfide(APDS) rather than 4,4′-dimercaptoazobenzene(DMAB) was achieved in water by visible irradiation,...

Synthesis of blue light emitting copolymers by oxidative coupling reaction

2003 ◽  
Vol 135-136 ◽  
pp. 201-202 ◽  
Author(s):  
Yingfeng Yu ◽  
Minghai Wang ◽  
Wei Huang ◽  
Shanjun Li
Keyword(s):  
Blue Light ◽  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Light Emitting ◽  
Oxidative Coupling Reaction

ChemInform Abstract: On the Coupling Reaction of Lithium Azaenolates of Chiral Oxazolines with Carbonyl Compounds.

ChemInform ◽  
2010 ◽  
Vol 32 (45) ◽  
pp. no-no
Author(s):  
Saverio Florio ◽  
Vito Capriati ◽  
Renzo Luisi ◽  
Alessandro Abbotto ◽  
Daniel J. Pippel
Keyword(s):  
Carbonyl Compounds ◽  
Coupling Reaction

A New Entry to Carbocyclic Nucleosides: Oxidative Coupling Reaction of Cycloalkenylsilanes with a Nucleobase Mediated by Hypervalent Iodine Reagent

2008 ◽  
Vol 10 (16) ◽  
pp. 3449-3452 ◽  
Author(s):  
Yuichi Yoshimura ◽  
Masatoshi Ohta ◽  
Tatsushi Imahori ◽  
Tomozumi Imamichi ◽  
Hiroki Takahata
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Hypervalent Iodine ◽  
Carbocyclic Nucleosides ◽  
Oxidative Coupling Reaction ◽  
New Entry
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