C–C bond formation from alcohols and malonate half esters using borrowing hydrogen methodology

Pridmore, Simon J.; Williams, Jonathan M. J.

doi:10.1016/j.tetlet.2008.10.059

Cited by 55 publications

(19 citation statements)

References 25 publications

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“…Since then, great progress has been made in this area, allowing the reaction to be carried out under milder conditions,7j, 10 with broader substrate scope,7h or even in an enantioselective manner 7m. 11 Notable contributions have come from the groups of Beller,3, 7p,q,s, 12 Williams,7a,c,d,f,h,r,t–v,x, 13 Fujita,14 Kempe,7z, 10, 15 Martín‐Matute,16 Crabtree,17 Yus,7b, 18 Peris,7g Andersson,7j Milstein,19 Zhao7m, 11b and others 20. The strategy could be further extended to the cross coupling of amines as reported by the groups of Beller,7p,q Peris7g and Williams 7r.…”

Section: Methodsmentioning

confidence: 99%

Alkylation of Amines with Alcohols and Amines by a Single Catalyst under Mild Conditions

Zou

Wang

Smith

et al. 2015

Chemistry A European J

100

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An efficient catalytic system for the alkylation of amines with either alcohols or amines under mild conditions has been developed, using cyclometallated iridium complexes as catalysts. The method has broad substrate scope, allowing for the synthesis of a diverse range of secondary and tertiary amines with good to excellent yields. By controlling the ratio of substrates, both mono- and bis-alkylated amines can be obtained with high selectivity. In particular, methanol can be used as the alkylating reagent, affording N-methylated products selectively. A strong solvent effect is observed for the reaction.

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Section: Methodsmentioning

confidence: 99%

Alkylation of Amines with Alcohols and Amines by a Single Catalyst under Mild Conditions

Zou

Wang

Smith

et al. 2015

Chemistry A European J

100

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“…The sensitivity of our catalyst to the presence of the potential hydrogen accepting groups is not surprising and is a limitation of the method. [11,26] The formation of H 2 was not monitored routinely. However, the amount of dihydrogen evolved upon dehydrogenation of 1-phenylethanol to acetophenone in a sealed tube correlates well to the theoretical yield.…”

Section: Conditions (Any Loss Of Product Occurs During the Isolation)mentioning

confidence: 99%

Ligand–Metal Cooperation in PCP Pincer Complexes: Rational Design and Catalytic Activity in Acceptorless Dehydrogenation of Alcohols

et al. 2011

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A helping hand: The dibenzobarrelene‐based PC sp 3P pincer complex 1 was designed as a bifunctional catalyst for the acceptorless dehydrogenation of alcohols. The mechanism of the H2 release involves interaction between the hydride ligand and the acidic sidearm in the intermediate 2 (red O, yellow Cl, green P, blue Ir). The feasibility of the complete catalytic cycle was studied using a stoichiometric model and the reaction was subsequently realized in a catalytic fashion.

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“…In fact, the metal‐catalyzed hydrogen‐borrowing strategy provides prominence benefit including high atom efficiency, low cost, water as by‐product etc., than other methods . Recently, the core moiety of the pharmaceutically active intermediate was successively synthesized through hydrogen auto‐transfer process .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structures of Arene Ruthenium (II)–NHC Complexes: Efficient Catalytic α‐alkylation of ketones via Hydrogen Auto Transfer Reaction

Balamurugan

Balaji

Ramesh

et al. 2018

Applied Organom Chemis

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A panel of six new arene Ru (II)-NHC complexes 2a-f, (NHC = 1,6dimethyl)benzimidazolin-2-ylidene 1a, 1,3-dicyclohexylmethyl-(5,6-dimethyl) benzimidazolin-2-ylidene 1b and 1,3-dibenzyl-(5,6-dimethyl)benzimidazolin-2-ylidene 1c) were synthesized from the transmetallation reaction of Ag-NHC with [(η 6 -arene)RuCl 2 ] 2 and characterized. The ruthenium (II)-NHC complexes 2a-f were developed as effective catalysts for α-alkylation of ketones and synthesis of bioactive quinoline using primary/amino alcohols as coupling partners respectively. The reactions were performed with 0.5 mol% catalyst load in 8 h under aerobic condition and the maximum yield was up to 96%. Besides, the different alkyl wingtips on NHC and arene moieties were studied to differentiate the catalytic robustness of the complexes in the transformations.

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C–C bond formation from alcohols and malonate half esters using borrowing hydrogen methodology

Cited by 55 publications

References 25 publications

Alkylation of Amines with Alcohols and Amines by a Single Catalyst under Mild Conditions

Alkylation of Amines with Alcohols and Amines by a Single Catalyst under Mild Conditions

Ligand–Metal Cooperation in PCP Pincer Complexes: Rational Design and Catalytic Activity in Acceptorless Dehydrogenation of Alcohols

Synthesis and Structures of Arene Ruthenium (II)–NHC Complexes: Efficient Catalytic α‐alkylation of ketones via Hydrogen Auto Transfer Reaction

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