Electrocatalytic coupling of aryl halides with (1,2-bis(di-2-propylphosphino)benzene)nickel(0)

Fox, Marye Anne; Chandler, Daniel A.; Lee, Changjin

doi:10.1021/jo00010a014

Cited by 40 publications

(24 citation statements)

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“…The indolin‐2‐one core structure can be formed by cyclization of N ‐arylacrylamide compounds. These ring‐closing reactions have been well investigated, and several methodologies have already been developed, including transition‐metal‐catalyzed Heck‐like couplings, Suzuki‐type reactions, oxidative palladium‐catalyzed cyclizations, oxidative cyclizations, and intramolecular radical ring closures initiated electrochemically with chemical initiators {e.g., 2,2′‐azobisisobutyronitrile (AIBN), tert ‐butyl hydroperoxide (TBHP), Bu 3 SnH, Langlois' salt [F 3 CS(O)ONa]} or by UV and visible light . Remarkably, there are significant examples of Ir‐ and Ru‐photocatalyzed cyclization reactions of N ‐arylacrylamide derivatives to oxazolines, benzoxazines, 3,4‐disubstituted dihydroquinolinones,, 1‐azaspiro[4.5]decanes, and indolin‐2‐ones.…”

Section: Introductionmentioning

confidence: 99%

Erythrosine B Catalyzed Visible‐Light Photoredox Arylation–Cyclization of N‐Alkyl‐N‐aryl‐2‐(trifluoromethyl)acrylamides to 3‐(Trifluoromethyl)indolin‐2‐one Derivatives

et al. 2017

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Section: Introductionmentioning

confidence: 99%

Erythrosine B Catalyzed Visible‐Light Photoredox Arylation–Cyclization of N‐Alkyl‐N‐aryl‐2‐(trifluoromethyl)acrylamides to 3‐(Trifluoromethyl)indolin‐2‐one Derivatives

et al. 2017

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“…Early reports by Jennings [83] were followed by mechanistic investigations by PØrichon and co-workers, [84] and the applied catalyst was further improved by Foxand co-workers. [85] Here,t he reactions were carried out under argon atmosphere in ad ivided cell. Theu se of ac arbon cloth cathode offered al arge surface area while the applied sacrificial lithium anodes seem to be untypical.…”

Section: Cathodic Couplings Of Prefunctionalized Arenesmentioning

confidence: 99%

Elektrifizierung der organischen Synthese

et al. 2018

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Die direkte Nutzung von Elektrizität für die organische Synthese erlebt derzeit eine Renaissance. Von den eher syntheseorientierten Laboratorien, die auf diesem Gebiet arbeiten, werden neuartige oder althergebrachte Konzepte genutzt, um den Weg von der Nischentechnologie zu breiteren Anwendungen zu ebnen. Da nur Elektronen als Reagens genutzt werden, wird die Bildung von Abfallreagentien effizient vermieden. Darüber hinaus können stöchiometrische Reagentien regeneriert werden und ermöglichen eine elektrokatalysierte Umsetzung. Die Anwendung von elektroorganischen Transformationen ist jedoch mehr als nur die Minimierung des Abfallaufkommens; sie führt vielmehr zu inhärent sicheren Prozessen, zur Abkürzung vieler Synthesestufen, zu milderen Reaktionsbedingungen, zu alternativen Zugängen zu gewünschten Struktureinheiten sowie zur Schaffung neuer Bereiche für geistiges Eigentum (Patente). Wenn die verwendete Elektrizität aus regenerativen Ressourcen stammt, kann dieser Stromüberschuss direkt als terminales Oxidations‐ oder Reduktionsmittel eingesetzt werden, was eine äußerst nachhaltige und damit hochattraktive Technologie darstellt. Dieser Aufsatz gibt einen Überblick über die jüngsten Entwicklungen auf dem Gebiet der elektrochemischen Synthese, welche die Zukunft dieses stark aufstrebenden Gebietes beeinflussen werden.

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“…Depending on the substrate, the mediator, and the reaction conditions, mixtures of the dimer and the disproportionation products of the alkyl radical intermediate were formed (cf. In many of the reactions examined, dehalogenation of the substrate predominated over coupling [162][163][164][165]. The same group [161] reported that traces of metal ions (e.g., Cu 2+ ) in the catholyte improved the current density and selectivity for several cathodic processes, and thus the conversion of trichloroacetic acid to chloroacetic acid.…”

Section: Electrochemical Reductionsmentioning

confidence: 99%

“…Usually, RH is formed by hydrogen abstraction from the reducing agent or the solvent [36,91,150,157,169,173,179,198], but dimerization [173,194,198], disproportionation (formation of RH and R(-H) simultaneously) [155,[158][159][160]170], or rearrangement [43,49,55,165,194] can also take place. Usually, RH is formed by hydrogen abstraction from the reducing agent or the solvent [36,91,150,157,169,173,179,198], but dimerization [173,194,198], disproportionation (formation of RH and R(-H) simultaneously) [155,[158][159][160]170], or rearrangement [43,49,55,165,194] can also take place.…”

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confidence: 99%

Dehalogenation Reactions

and¹,

Simon²

2006

The Handbook of Homogeneous Hydrogenation

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Reductive dehalogenation -one of the earliest reactions described in the organic chemical literature -has achieved special significance since the 1980s when the harmful properties of numerous halogenated (chiefly chlorinated) hydrocarbons became clear. The identification of methods capable of neutralizing or, at least, diminishing these dangers, remains a major challenge for chemistry. It is reasonable to convert stocks of the prohibited chemicals (e.g., polychlorobiphenyls, PCBs; chlorofluorocarbons, CFCs) to valuable products as far as possible. At the same time, the halogen-containing wastes should be detoxified by degradation. During the past two decades, the mainly heterogeneous (but also homogeneous) catalytic dehalogenation provided a major share towards solving these problems. Within this period, substantial progress was also made in the application of these reactions in organic syntheses.Hydrodehalogenation -that is, hydrogenolysis of the carbon-halogen bondinvolves the displacement of a halogen bound to carbon by a hydrogen atom. This chapter is devoted to dehalogenations mediated by transition-metal complexes (Eq. (1)): ÀC j j ÀX reducing agent L n Mj 3 ÀC j j ÀH Y 1 where X = F, Cl, Br, I, and [L n M] = a transition metal complex. The use of a wide variety of reducing agents (H 2 , hydrides of metals and metalloids, organic reductants, etc.) under the most diverse reaction conditions (e.g., one-or two-phase systems) has been reported. Organic halides have also been reduced by electrochemical and photochemical methods in the presence of compounds of the type [L n M]. Reductive transformations of organic halides not relevant to Eq.(1) (e.g., coupling reactions) and dehalogenation of acyl halides will not be included here. 513The Handbook of Homogeneous Hydrogenation. Edited by J. G. de Vries and C. J. ElsevierThe reactivity of the carbon-halogen bond in Eq. (1) depends on several factors: · the nature of the halogen atom; · the environment of the halogen atom in the molecule; and · the reagents and conditions used in Eq. (1) [1].The order of reactivity of the C-X bond (generally: I > Br > Cl > F) is consistent with its strength. For instance, the experimentally found dissociation energies for phenyl halides (D Ph-X ) are 528, 402, 339, and 272 kJ mol -1 at 298 K for X = F, Cl, Br, and I, respectively [2]. Consequently, catalytic defluorination in the literature is comparatively rare. The different reactivity of the C-X bonds renders possible the selective dehalogenation of compounds containing two dissimilar halides, leaving intact the stronger C-X bond.

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Electrocatalytic coupling of aryl halides with (1,2-bis(di-2-propylphosphino)benzene)nickel(0)

Cited by 40 publications

References 5 publications

Erythrosine B Catalyzed Visible‐Light Photoredox Arylation–Cyclization of N‐Alkyl‐N‐aryl‐2‐(trifluoromethyl)acrylamides to 3‐(Trifluoromethyl)indolin‐2‐one Derivatives

Erythrosine B Catalyzed Visible‐Light Photoredox Arylation–Cyclization of N‐Alkyl‐N‐aryl‐2‐(trifluoromethyl)acrylamides to 3‐(Trifluoromethyl)indolin‐2‐one Derivatives

Elektrifizierung der organischen Synthese

Dehalogenation Reactions

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