Ruthenium-Catalyzed Regioselectiveα-Alkylation of Ketones: The First Alkyl-Group Transfer from Trialkylamines to theα-C Atom of Ketones

Cho, Chan Sik; Kim, Bok Tae; Lee, Myung Jin; Kim, Tae‐Jeong; Shim, Sang Chul

doi:10.1002/1521-3773(20010302)40:5<958::aid-anie958>3.0.co;2-4

Cited by 67 publications

(3 citation statements)

References 26 publications

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“…Cho et al reported the α-alkylation of ketones with trialkylamines as hydrogen donors, in which the alkyl group was transferred by the in situ prepared catalyst of ruthenium (RuCl 3 and PPh 3 ) to give the final product.…”

Section: Borrowing Hydrogen Methodology In Homogeneous Catalysismentioning

confidence: 99%

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: Borrowing Hydrogen Methodology In Homogeneous Catalysismentioning

confidence: 99%

Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis

2018

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“…Transition metal‐catalyzed transfer hydrogenations of ketones to alkanes have also been developed in order to overcome drawbacks, such as the requirement for strong acidic and basic conditions, in such conventional reductions . As part of our continuing studies directed towards transition metal‐catalyzed transfer hydrogenation accompanied by carbon–carbon bond‐forming reactions, we found that alkyl groups of trialkylamines are regioselectively transferred to the α‐carbon atom of ketones in the presence of a ruthenium catalyst (α‐alkylation of ketones by trialkylamines) . The present work originated during the course of the extension of this protocol to seek for a catalyst alternative which exhibits similar catalytic activity.…”

Section: Introductionmentioning

confidence: 99%

Transfer hydrogenation of ketones to alkanes using tributylamine under heterogeneous Pd/C catalysis

Kim

Cho

Kim

2014

Applied Organom Chemis

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“…1 Besides conventional reduction routes, recently, catalytic transfer hydrogenation has been attempted because of the facility and efficiency of reaction. 2 During the course of our ongoing studies on ruthenium catalysis, [3][4][5] we recently found an unusual type of ruthenium-catalysed transfer hydrogenation of ketones by alcohols accompanied by C-C coupling under KOH. 6,7 In connection with this report, Imai et al partly reported that dioxane can be used as a hydrogen donor in rutheniumcatalysed transfer hydrogenation of aldehyde, giving a low yield of alcohol.…”

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confidence: 99%