Pd-catalyzed decarboxylative cross-coupling of perfluorobenzoic acids with simple arenes

Luo, Haiqing; Dong, Wen; Loh, Teck‐Peng

doi:10.1016/j.tetlet.2013.03.086

Cited by 35 publications

(8 citation statements)

References 42 publications

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“…Luo et al realised that simple arenes could also be used as coupling partners (Scheme ) . Unfortunately, the arene component was required in solvent quantities and the benzoic acid component was limited to highly activated polyfluorinated substrates.…”

Section: Decarboxylative C–co2h/c–h Couplingmentioning

confidence: 99%

Recent Progress in Decarboxylative Oxidative Cross‐Coupling for Biaryl Synthesis

2017

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The beginning of the 21st century has seen tremendous growth in the field of decarboxylative activation. Benzoic acid derivatives are now recognised as atom‐economic alternatives to traditional cross‐coupling partners, and they also benefit from being inexpensive, readily available and shelf‐stable reagents. In this microreview we discuss recent developments in the coupling of benzoic acid derivatives either with an arene or with a second benzoic acid derivative, a process often termed decarboxylative oxidative cross‐coupling. These procedures offer great promise for the development of highly selective and atom‐economic cross‐couplings.

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Section: Decarboxylative C–co2h/c–h Couplingmentioning

confidence: 99%

Recent Progress in Decarboxylative Oxidative Cross‐Coupling for Biaryl Synthesis

2017

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“…If Ni 2 P loading amount was increased to 6.3 % (entry 6), the conversion efficiency (88.0 %) of p ‐xylene was declined, and the selectivity to 1,2‐di‐ p ‐tolylethane was also reduced to 35.3 %. We tentatively attributed the decreased catalytic conversion to the excess Ni 2 P nanoparticles covering on the surface of Cd 0.5 Zn 0.5 S and shielding the catalyst from incident light . In the absence of catalyst or light, not any products were detected in the reaction system (entries 7 and 8).…”

Section: Resultsmentioning

confidence: 93%

Visible‐Light‐Driven Self‐Coupling of Methylarenes Catalyzed by Ni₂P@Cd_0.5Zn_0.5S Nanoparticles

Yang

Zhang

et al. 2019

Zeitschrift anorg allge chemie

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The Ni 2 P@Cd 0.5 Zn 0.5 S nanoparticles photocatalyzed selfcoupling of p-xylene was reported here, and the corresponding coupling product 1,2-di-p-tolylethane was obtained. The reaction could be extended to toluene derivatives with electron-donating and electronwithdrawing substituents. Ni 2 P@Cd 0.5 Zn 0.5 S nanoparticles had already been characterized by XRD, ICP-AES, SEM, TEM, UV/Vis, FL, XPS. 1384The Mott-Schottky curves of Ni 2 P@Cd 0.5 Zn 0.5 S were made through electrochemical methods. An active carbon free-radical was captured through ESR measurement under irradiation. The research demonstrated this photocatalytic system feasible for the self-coupling reaction of toluene derivatives. Figure 3. (a) UV/Vis DRS of Cd 0.5 Zn 0.5 S and Ni 2 P@Cd 0.5 Zn 0.5 S from 0 to 6.3 %; (b) photoluminescence properties of Cd 0.5 Zn 0.5 S and Ni 2 P@Cd 0.5 Zn 0.5 S (5%).

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“…As an example for the construction of fluorobiphenyls, Luo recently explored an approach capable of decarboxylative coupling with perfluorobenzoic acids and benzene, toluene, chlorobenzene, or xylene, applying a Pd/Ag bimetallic system (Scheme 36). 54 The major disadvantages of this method lie in the narrow substrate scope with both fluorobenzoic acids and simple arenes as well as low reactivity.…”

Section: Decarboxylative Csp 2 −H Bond Functionalizationmentioning

confidence: 99%

Metal-Catalyzed Decarboxylative C–H Functionalization

et al. 2017

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C-H bond activation and decarboxylation are two significant processes in organic synthesis. The combination of these processes provides a novel synthetic strategy, that is, decarboxylative C-H bond functionalization. Considerable attention has been focused on such an active research field. This review offers an overview of the utility of decarboxylative C-H bond functionalization in the synthesis of various organic compounds, such as styrenes, chalcones, biaryls, and heterocycles, covering most of the recent advances of the decarboxylative functionalization of Csp-H, Csp-H, and Csp-H bonds, as well as their scopes, limitations, practical applications, and synthetic potentials.

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Pd-catalyzed decarboxylative cross-coupling of perfluorobenzoic acids with simple arenes

Cited by 35 publications

References 42 publications

Recent Progress in Decarboxylative Oxidative Cross‐Coupling for Biaryl Synthesis

Recent Progress in Decarboxylative Oxidative Cross‐Coupling for Biaryl Synthesis

Visible‐Light‐Driven Self‐Coupling of Methylarenes Catalyzed by Ni₂P@Cd_0.5Zn_0.5S Nanoparticles

Metal-Catalyzed Decarboxylative C–H Functionalization

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Pd-catalyzed decarboxylative cross-coupling of perfluorobenzoic acids with simple arenes

Cited by 35 publications

References 42 publications

Recent Progress in Decarboxylative Oxidative Cross‐Coupling for Biaryl Synthesis

Recent Progress in Decarboxylative Oxidative Cross‐Coupling for Biaryl Synthesis

Visible‐Light‐Driven Self‐Coupling of Methylarenes Catalyzed by Ni2P@Cd0.5Zn0.5S Nanoparticles

Metal-Catalyzed Decarboxylative C–H Functionalization

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Visible‐Light‐Driven Self‐Coupling of Methylarenes Catalyzed by Ni₂P@Cd_0.5Zn_0.5S Nanoparticles