Pd/C‐Catalyzed Alkylation of Heterocyclic Nucleophiles with Alcohols through the “Borrowing Hydrogen” Process

Putra, Anggi Eka; Oe, Yohei; Ohta, Tetsuo

doi:10.1002/ejoc.201501030

Cited by 28 publications

(11 citation statements)

References 50 publications

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“…Besides, it was possible to carry out the process at lower temperatures. 319,320 In a recent and interesting approach, the preparation of a DMF-stabilized iridium nanocluster as methylation catalyst has been described. The corresponding micrographs of HR-TEM showed that the small Ir clusters had an average diameter of 1− 1.5 nm and were stabilized with DMF.…”

Section: Activation Of Alcoholsmentioning

confidence: 99%

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Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis

2018

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The borrowing hydrogen (BH) principle, also called hydrogen auto-transfer, is a powerful approach which combines transfer hydrogenation (avoiding the direct use of molecular hydrogen) with one or more intermediate reactions to synthesize more complex molecules without the need for tedious separation or isolation processes. The strategy which usually relies on three steps, (i) dehydrogenation, (ii) intermediate reaction, and (iii) hydrogenation, is an excellent and well-recognized process from the synthetic, economic, and environmental point of view. In this context, the objective of the present review is to give a global overview on the topic starting from those contributions published prior to the emergence of the BH concept to the most recent and current research under the term of BH catalysis. Two main subareas of the topic (homogeneous and heterogeneous catalysis) have been identified, from which three subheadings based on the source of the electrophile (alkanes, alcohols, and amines) have been considered. Then the type of bond being formed (carbon-carbon and carbon heteroatom) has been taken into account to end-up with the intermediate reaction working in tandem with the metal-catalyzed hydrogenation/dehydrogenation step. The review has been completed with the more recent advances in asymmetric catalysis using the BH strategy.

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Section: Activation Of Alcoholsmentioning

confidence: 99%

“…Furthermore, the catalyst could be recycled up to five times with a negligible loss of efficiency ( Figure 10). 320 3. (209) in the presence of Ni nanoparticles.…”

Section: Activation Of Alcoholsmentioning

confidence: 99%

Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis

2018

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“…For instance, Ohta et al reported the Pd/C‐catalyzed alkylation of heterocyclic nucleophiles with various alcohols, via the ‘borrowing‐hydrogen’ reaction in 1,4‐dioxane at 120 °C [Eq. (64)] . Additionally, 4‐hydroxy‐1‐methylquinolinone, barbituric acids, and oxindole are also suitable for this alkylation reaction.…”

Section: Applications Of Pd/cmentioning

confidence: 99%

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Liu

Astruc

2018

Adv Synth Catal

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Palladium on charcoal( Pd/C)h as lots of salient merits:( i) it is ac heap andc ommercial source of palladium, (ii)i ts hows efficientc atalytic activity even without ligands,( iii)a saheterogeneous catalyst it is easily recycledm any times by simple filtration,a nd (iv) it is applicablet oag reat number of reactions and substrates,a lthough it is eventually less efficient than homogeneous Pd catalysts containing some sophisticated ligands.T hisr eview recalls the main background ands ummarizes the progress made essentially during the last twelve years in Pd/C-catalyzed organic synthesis since the reviews by Felpins group andSekiin2 006.

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“…7 Furthermore, Madsen et al and Hong et al reported Ru-NHC catalyzed direct amide syntheses using alcohols and amines. Very limited reports exist for the α-alkylation of amides 8 catalyzed by air sensitive cooperative pincer-type complexes.…”

Section: Introductionmentioning

confidence: 99%

Ru-NHC Catalyzed Domino Reaction of Carbonyl Compounds and Alcohols: A Short Synthesis of Donaxaridine

et al. 2017

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Direct α-alkylation of amides and the synthesis of C3-alkylated 3-hydroxyindolin-2-one/2-substituted-2-hydroxy-3,4-dihydronaphthalen-1(2 H )-one derivatives from 2-oxindole/1-teralone were reported using primary alcohols in the presence of Ru-NHC catalyst in a one pot condition under the borrowing hydrogen method. In the case of inert conditions, 2-oxindole/1-teralone exclusively forms the C3-alkylated product. Whereas, allowing this reaction mixture to occur under an air atmosphere predominantly forms C3-alkylated 3-hydroxyindolin-2-one via domino C–H alkylation and aerobic C–H hydroxylation. This Ru-NHC catalyst is easily accessible, air stable, and phosphine free. Using this method, synthesis of 2-oxindole based natural products such as Donaxaridine was accomplished.

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Pd/C‐Catalyzed Alkylation of Heterocyclic Nucleophiles with Alcohols through the “Borrowing Hydrogen” Process

Cited by 28 publications

References 50 publications

Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis

Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Ru-NHC Catalyzed Domino Reaction of Carbonyl Compounds and Alcohols: A Short Synthesis of Donaxaridine

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