Acceptorless Alcohol Dehydrogenation: A Mechanistic Perspective

Pandey, Pragati; Dutta, Indranil; Bera, Jitendra K.

doi:10.1007/s40010-016-0296-7

Cited by 31 publications

(15 citation statements)

References 146 publications

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“…According to the literature, substrate does not bind directly to the metal center in the outer sphere mechanism, but rather a synergistic interaction of the metal and ligand with alcohol created the product, which is supported by the control experiments (Table 3). [53,54] The activity of the ligand and metal precursor was compared to that of the Fc−Ru catalyst. [RuCl 2 (η 6 ‐ p ‐cymene)] 2 and ligand L 4 showed 84 and 51 % selectivity, respectively towards 1,2‐disubstituted benzimidazole.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 1,2‐Disubstituted Benzimidazoles via Acceptorless Dehydrogenative Coupling Using Ru(II)‐Arene Catalysts Containing Ferrocene Thiosemicarbazone

Sindhuja

Bhuvanesh

et al. 2022

Eur J Inorg Chem

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The catalytic activity of Ru(II)-arene complexes containing ferrocene thiosemicarbazone (Fc-TSC) ligands was investigated towards the selective synthesis of 1,2-disubstituted benzimidazoles via acceptorless dehydrogenative coupling of diamines with primary alcohols. A series of Ru(II)-p-cymene complexes (1-4) containing Fc-TSC ligands (L 1 -L 4 ) were synthesized and characterized. From single crystal X-ray crystallographic studies, the molecular structures of L 3 and 4 were confirmed. The influence of electronic effect of ligands on the catalytic activity of their complexes was studied. The activity of good performer i. e. 4 was compared with that of its benzene counterpart (5). The catalysis was extended to aromatic, aliphatic and heterocyclic substituted primary alcohols, and phenylenediamines with electron-donating or -withdrawing substituents. Overall, synthesis of 1,2-disubstituted benzimidazoles was accomplished with good to moderate yields, with hydrogen and water as only by-products.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 1,2‐Disubstituted Benzimidazoles via Acceptorless Dehydrogenative Coupling Using Ru(II)‐Arene Catalysts Containing Ferrocene Thiosemicarbazone

Sindhuja

Bhuvanesh

et al. 2022

Eur J Inorg Chem

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“…A bimetallic cooperative mechanism on the same di‐palladium platform operating with substrate addition and product elimination has been proposed to explain the enhanced catalytic activity of complex 25 . Dinuclear ruthenium complexes of type 26 bearing NHC‐functionalized 1,8‐naphthyridine ligand have also been investigated by the same research group [50,52] . These dinuclear ruthenium complexes show both metal‐ligand and with metal‐metal cooperation in the formation reaction of imine from respective alcohols via dehydrogenative coupling (Scheme 9).…”

Section: Cooperative Effects In Homo‐multimetallic Complexes With Short Metal‐metal Distancesmentioning

confidence: 99%

“…One forward step towards the highly challenging design of suitable ligands to pursue enhanced bimetallic catalysis has been taken by Bera and co‐workers, [50] who have investigated the catalytic activity of a dinuclear palladium(II) complexes having a direct Pd−Pd bond. An amide‐linked naphthyridine‐ferrocene hybrid building block was used to accommodate both palladium atoms in close proximity within the same molecule (Scheme 9).…”

Section: Cooperative Effects In Homo‐multimetallic Complexes With Short Metal‐metal Distancesmentioning

confidence: 99%

Cooperative Effects in Multimetallic Complexes Applied in Catalysis

et al. 2021

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The field of multimetallic catalysis is rapidly developing and some multimetallic complexes catalyze organic transformations to yield the desired products in more efficient ways owing to the combined action of different metals in a cooperative fashion. This Concept article describes the recent advances of cooperative catalysis playing in multimetallic systems such as homo-multimetallic complexes with short metal-metal distances, homo-multimetallic complexes with long metal-metal distances, hetero-multimetallic complexes and metallocenebased multimetallic complexes with special attention towards redox-switchable catalysis. Examples are illustrated in which the use of multimetallic complexes show clear enhancement of catalytic outcomes when compared with the sum of their corresponding mononuclear counterparts. Furthermore, several examples are discussed showing the effects of electronic communication in cooperative systems.

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“…Hydrogen transfer methods constitute an attractive approach for many synthetic transformations. − Among these, reduction processes are more well-established. − Hydrogen transfer oxidation methods have also evolved, with the development of new catalysts, employing aqueous media, supported catalysts and in the absence of hydrogen acceptors. − Most notably, Bäckvall’s group has implemented procedures for hydrogen transfer oxidation employing commercial catalysts, and a base, to achieve high yields, and with good functional group compatibility. , …”

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confidence: 99%

Chemoselective Continuous Ru-Catalyzed Hydrogen-Transfer Oppenauer-Type Oxidation of Secondary Alcohols

Labes

Battilocchio

Mateos

et al. 2017

Org. Process Res. Dev.

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A continuous flow method for the selective oxidation of secondary alcohols is reported. The method is based on an Oppenauer-type ruthenium-catalyzed hydrogen-transfer process that uses acetone as both solvent and oxidant. The process utilizes a low loading (1 mol%) of the commercially available ruthenium catalyst [Ru(p-cymene)Cl2]2 and triethylamine as a base and can be successfully applied to a range of different substrates, with a good level of functional group tolerance.

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Acceptorless Alcohol Dehydrogenation: A Mechanistic Perspective

Cited by 31 publications

References 146 publications

Synthesis of 1,2‐Disubstituted Benzimidazoles via Acceptorless Dehydrogenative Coupling Using Ru(II)‐Arene Catalysts Containing Ferrocene Thiosemicarbazone

Synthesis of 1,2‐Disubstituted Benzimidazoles via Acceptorless Dehydrogenative Coupling Using Ru(II)‐Arene Catalysts Containing Ferrocene Thiosemicarbazone

Cooperative Effects in Multimetallic Complexes Applied in Catalysis

Chemoselective Continuous Ru-Catalyzed Hydrogen-Transfer Oppenauer-Type Oxidation of Secondary Alcohols

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