Water dispersed gold nanoparticles catalyzed aerobic oxidative cross-dehydrogenative coupling: An efficient synthesis of α-ketoamides in water

Thirukovela, Narasimha Swamy; Balaboina, Ramesh; Vadde, Ramakrishna; Vasam, Chandra Sekhar

doi:10.1016/j.tetlet.2018.08.042

Cited by 20 publications

(7 citation statements)

References 71 publications

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“…Heterogenous catalysts have been widely employed for catalytic oxidative amidation and can have superior substrate scope and milder conditions than their homogenous counterparts. A selected example is a heterogeneous gold catalyst supported on hydroxyapatite was shown to be able oxidatively couple benzyl and alkyl alcohols and aryl and alkyl amines to forge amides under mild aqueous conditions at 40 C. [140] Gold nanoparticles have also been shown to be capable of amidating (hetero)aryl, alkyl [141] and α-keto aldehydes [142] with alkyl amines with sub-ambient temperatures to mild heating (respectively) in aqueous solutions under an atmosphere of O 2 . The authors of the former study noted that the size of the nanoparticles had a large impact on the ability of the reaction to favor amidation over imine formation, with the largest particles being most selective for amidation.…”

Section: Heterogenous Catalystsmentioning

confidence: 99%

Recent developments in catalytic amide bond formation

Todorovic

Perrin

2020

Peptide Science

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Amide bond forming reactions are critical for both polypeptide synthesis and medicinal chemistry. Most current approaches for amidation employ stoichiometric activating agents, but such methods are neither atom economical nor synthetically elegant. Catalytic approaches for amidation are potentially green and more ideal substitutes for current standard methods and thus are the subject of this review. Such methods face significant thermodynamic and kinetic barriers and have, as a result, historically

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Section: Heterogenous Catalystsmentioning

confidence: 99%

Recent developments in catalytic amide bond formation

Todorovic

Perrin

2020

Peptide Science

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“…Easy product isolation, recyclable catalysts, mild reaction conditions, and a broad scope of substrates gave it significant advantages. Vasam and co-workers [62] developed gold nanoparticles-catalyzed aerobic oxidation CDC reaction, which could catalyze the synthesis of biologically important α-ketoamides from α-ketoaldehydes and secondary amines via water dispersed AuNPs (PEG-AuNPs, 5 nm, use the strong reducing agent sodium borohydride at room temperature to produce Au NPs with a mean diameter of 5 nm) [Eq. (47)].…”

Section: Transition-metal Catalysismentioning

confidence: 99%

Recent Advances in Cross‐Dehydrogenative Couplings (CDC) of C−H Bond in Aqueous Media

Peng

Dong

2021

Adv Synth Catal

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To develop highly efficient synthetic reactions is quite important in organic chemistry. Cross dehydrogenative couplings (CDC) utilize C−H bonds of substrates to construct new C−X (X=C, S, O, N, P) bonds. For CDC, the pre‐functionalization of reaction substrates can be avoided and the C−X (X=C, S, O, N, P) bonds can be newly formed by simple and efficient synthesis routes. Meanwhile, water is increasingly used as a substitute for organic solvents in cross‐dehydrogenative coupling because of its rich content, non‐toxicity, and non‐ flammability. In recent years, organic chemists are devoted their efforts to explore the cross dehydrogenative couplings (CDC) in aqueous phase which feature high atom utilization rate and environmental friendliness. Herein, we summarized the recent advances in the construction of C−C, C−S, C−O, C−N, and C−P bonds through CDC reactions of C−H bonds in water.

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“…As shown in Scheme 1, various metal-based catalysts have been reported for the synthesis of a-ketoamides by different synthetic methods. However, the disadvantages of using these methods are the use of a catalyst with metals such as Au, 10 Cu 11 , and Pd 12 , of which some metals are toxic and some are expensive. Sekar et al 13 reported a one-pot two-step synthesis of a-ketoamides from a-ketoalcohols using Fe(OAc) 2 in the presence of pyridine & TEMPO in acetonitrile as a solvent.…”

Section: Introductionmentioning

confidence: 99%