Highly Efficient Ruthenium(II) Porphyrin Catalyzed Amidation of Aldehydes

Chang, Joyce Wei Wei; Chan, Philip Wai Hong

doi:10.1002/anie.200704695

Cited by 159 publications

(71 citation statements)

References 48 publications

(10 reference statements)

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“…Synthesis of amides is mostly based on activated acid derivatives (acid chlorides and anhydrides) or rearrangement reactions induced by an acid or base 72), 73) . Alternative procedures include the Staudinger ligation 74) , aminocarbonylation of aryl halides 75) , oxidative amidation of aldehydes 76) , and amidation of alcohols with excess amount of hydrogen acceptor 77) . However, all these methods require stoichiometric amounts of various reagents and lead to equimolar amounts of byproducts.…”

Section: Coupling Of Alcohols With Amines To Formmentioning

confidence: 99%

Silver Cluster Catalysts for Green Organic Synthesis

Shimizu

Satsuma

2011

J. Jpn. Petrol. Inst.

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Development of platinum-group-metal (PGM)-free catalysts for green chemical synthesis is an important topic in synthetic catalysis, because PGM will soon be in short supply in the near future. Our group has paid attention to the catalytic functions of Ag clusters. Here, we summarize our recent work on size-and support-specific catalysis of Ag clusters for green organic synthesis. Ag clusters supported on Al2O3 act as effective heterogeneous catalysts for (1) oxidant-free dehydrogenation of alcohols to carbonyl compounds, (2) coupling of alcohols with amines to form amides and H2, (3) N-alkylation of anilines with alcohols, (4) C _ C cross-coupling reaction of alcohols, (5) selective hydrogenation of nitroaromatics, and (6) direct synthesis of N-substituted anilines from nitroaromatics and alcohols. To establish a catalyst design concept, effects of Ag particle size and acid-base character of support oxides are investigated. The structure-activity relationships for all reactions show similar tendencies; metallic Ag clusters with smaller size and acid-base bifunctional nature of the support oxide are preferable. We propose that cooperation between coordinatively unsaturated Ag sites of Ag clusters and acidbase pair sites at the metal-support interface is a key concept for the design of Ag cluster catalysts for the above reactions.

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Section: Coupling Of Alcohols With Amines To Formmentioning

confidence: 99%

Silver Cluster Catalysts for Green Organic Synthesis

Shimizu

Satsuma

2011

J. Jpn. Petrol. Inst.

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“…Various metal complexes have been reported for the oxidative amidation of aldehydes. [9] Scheme 1. Proposed mechanism.…”

Section: Introductionmentioning

confidence: 99%

“…Amides are typically synthesized by coupling of activated carboxylic acid derivatives with amines. [2] Alternative strategies toward the synthesis of amides are the Staudinger reaction, [3] the Schmidt reaction, [4] Beckmann rearrangement, [5] aminocarbonylation of haloarenes, [6] alkenes [7] and alkynes, [8] oxidative amidation of aldehydes, [9] hydrative amide synthesis with alkynes [10] and the amidation of thio acids with azides. [11] However, most of these methods require an equimolar amount of various reagents and generate larger amounts of by-products as waste.…”

Section: Introductionmentioning

confidence: 99%

Direct Amide Synthesis from Alcohols and Amines by Phosphine‐Free Ruthenium Catalyst Systems

et al. 2009

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Amides are synthesized directly from alcohols and amines in high yields using an in situ generated catalyst from easily available ruthenium complexes such as the (p-cymene, an N-heterocyclic carbene (NHC) ligand, and a nitrogen containing L-type ligand such as acetonitrile. The phosphine-free catalyst systems showed improved or comparable activity compared to previous phosphine-based catalytic systems. The in situ generated catalyst from [RuA C H T U N G T R E N N U N G (benzene)Cl 2 ] 2 , an NHC ligand, and acetonitrile showed excellent activity toward reactions with cyclic secondary amines such as piperidine and morpholine.

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“…[5c,d] Recently, the rhodiumand ruthenium-catalyzed sulfamidation of aldehydes has been developed via a C À H activation strategy. [6] The copper-catalyzed three-component coupling of terminal alkynes, sulfonyl azides and water to form acylsulfonamides has been reported. [7] Every method above has it advantages and disadvantages, therefore it is still desirable to develop more convenient and efficient methods for the synthesis of imides and acylsulfonamides.…”

Section: Introductionmentioning

confidence: 99%