Oxidative coupling of Michael acceptors with aryl nucleophiles produced through rhodium-catalyzed C–C bond activation

2017 ◽  
Vol 15 (28) ◽  
pp. 5944-5948 ◽  
Author(s):  
Caroline E. Gregerson ◽  
Kathryn N. Trentadue ◽  
Erik J. T. Phipps ◽  
Janelle K. Kirsch ◽  
Katherine M. Reed ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Bond Activation ◽  
Cross Coupling ◽  
Michael Acceptors

C–C bond activation generates aryl nucleophiles for cross-coupling.

scholarly journals Cross‐Coupling of Aryl/Alkenyl Pivalates with Organozinc Reagents through Nickel‐Catalyzed CO Bond Activation under Mild Reaction Conditions

2009 ◽  
Vol 48 (8) ◽  
pp. 1351-1351
Author(s):  
Bi‐Jie Li ◽  
Yi‐Zhou Li ◽  
Xing‐Yu Lu ◽  
Jia Liu ◽  
Bing‐Tao Guan ◽  
...  
Keyword(s):  
Bond Activation ◽  
Cross Coupling ◽  
Reaction Conditions ◽  
Organozinc Reagents

scholarly journals DFT Study of Unstrained Ketone C-C Bond Activation via Rhodium(I)-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions

2019 ◽  
Author(s):  
Dengmengfei Xiao ◽  
Lili Zhao ◽  
Diego Andrada
Keyword(s):  
Density Functional ◽  
Bond Activation ◽  
Chemical Reactivity ◽  
Cross Coupling ◽  
Underlying Mechanism ◽  
Reductive Elimination ◽  
Coupling Reactions ◽  
Co Catalysts ◽  
Cross Coupling Reactions ◽  
Strain Model

Unstrained cyclic ketones can participate in cooperative Suzuki-Miyaura cross-coupling type reaction using rhodium(I)-based catalyst via C-C bond activation. The regioselectivity indicates a trend where the most substituted side is activated and it is controlled by the beta-substituents. In this work, Density Functional Theory (DFT) calculations have been carried out to disclose the underlying mechanism in the reaction of a ketone series and arylboronate using ylidene as ancillary ligand and pyridine as co-catalysts. The computed energies suggest the reductive elimination step with the highest energy while the reductive elimination has the highest energy barrier. By the means of the Activation Strain Model (ASM) of chemical reactivity, it is found that the ketone strain energy released on the oxidative addition does not control the relativity of the OA reactivity, but indeed is the interaction energy between Rh(I) and C-C bond the ruling effect. The effect of the beta-substituents on regioselectivity has been additionally studied.

ChemInform Abstract: Palladium-Catalyzed Cross-Coupling of Aryl Fluorides with N-Tosylhydrazones via C-F Bond Activation.

ChemInform ◽  
2015 ◽  
Vol 46 (52) ◽  
pp. no-no
Author(s):  
Haiqing Luo ◽  
Guojiao Wu ◽  
Shuai Xu ◽  
Kang Wang ◽  
Chaoqiang Wu ◽  
...  
Keyword(s):  
Bond Activation ◽  
Cross Coupling ◽  
Palladium Catalyzed

Palladium-Catalyzed/Lewis Acid-Promoted Alkene Dimerization and Cross-Coupling with AlcoholsviaCH Bond Activation

2008 ◽  
Vol 350 (4) ◽  
pp. 552-556 ◽  
Author(s):  
Yi-Jun Jiang ◽  
Yong-Qiang Tu ◽  
En Zhang ◽  
Shu-Yu Zhang ◽  
Ke Cao ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Bond Activation ◽  
Cross Coupling ◽  
Palladium Catalyzed

KI-Promoted Oxidative Coupling of Styrenes with Indoles under Metal-Free Conditions: Facile Access to C-3 Dicarbonyl Indoles

Synthesis ◽  
2019 ◽  
Vol 51 (18) ◽  
pp. 3511-3519
Author(s):  
Bochao Zhou ◽  
Shiyu Guo ◽  
Zheng Fang ◽  
Zhao Yang ◽  
Chengkou Liu ◽  
...  
Keyword(s):  
Efficient Method ◽  
Oxidative Coupling ◽  
Isotope Labeling ◽  
Cross Coupling ◽  
Metal Free ◽  
Broad Scope ◽  
Plausible Mechanism ◽  
Isotope Labeling Experiments

A new and efficient method for the synthesis of C-3 dicarbonyl indoles via oxidative cross-coupling of styrenes with indoles under metal-free conditions has been developed. Moreover, a broad scope of C-3 dicarbonyl indoles in moderate to good yields were obtained, and a plausible mechanism is proposed based on control and isotope-labeling experiments.

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.

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