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Relevant academic research and scientific papers

UV Assisted High-Efficient Synthesis of α-Ketoamides using Air Promoted by A Non-Metal Catalyst in Aqueous Solution

Presented here is the first example of UV (λ=210 nm) promoted procedure proceeding in aqueous media at room temperature using ambient air as the oxidant for efficient synthesis of an array of α-ketoamides of all types using a non-metal catalyst N-iodosuccinimide with a loading of 20 mol%. With UV, oxygen in the air was efficiently utilized as the green oxidant, some control experiments were carried out and a plausible mechanism was proposed, disclosing that in aqueous solution, the oxidation process was actually triggered by dioxygen radical anion (O2.?), while not molecular oxygen. A variety of secondary amines and primary amines as well as ammonia were employed as the amine moieties, and the desired product primary-, secondary-, and tertiary α-ketoamides were afforded in good to excellent yields of up to 96 %.

C-H/C-C Functionalization Approach to N-Fused Heterocycles from Saturated Azacycles

Herein we report the synthesis of substituted indolizidines and related N-fused bicycles from simple saturated cyclic amines through sequential C-H and C-C bond functionalizations. Inspired by the Norrish-Yang Type II reaction, C-H functionalization of azacycles is achieved by forming α-hydroxy-β-lactams from precursor α-ketoamide derivatives under mild, visible light conditions. Selective cleavage of the distal C(sp2)-C(sp3) bond in α-hydroxy-β-lactams using a Rh-complex leads to α-acyl intermediates which undergo sequential Rh-catalyzed decarbonylation, 1,4-addition to an electrophile, and aldol cyclization, to afford N-fused bicycles including indolizidines. Computational studies provide mechanistic insight into the observed positional selectivity of C-C cleavage, which depends strongly on the groups bound to Rh trans to the phosphine ligand.

Cu-Catalysed oxidative amidation of cinnamic acids/arylacetic acids with 2° amines: An efficient synthesis of α-ketoamides

A new and convenient copper-catalysed synthesis of α-ketoamides has been accomplished using readily available cinnamic acids/arylacetic acids and 2° amines in an open atmosphere. The reaction between cinnamic acid and amine involves the formation of enamine followed by its aerobic oxidation, whereas the reaction of arylacetic acid with amine involves amide formation followed by benzylic methylene oxidation.

Polymer supported triazine based palladium complex catalyzed double carbonylation reaction of halo aryl compounds for the synthesis of α-ketoamides

Novel polystyrene incorporated Palladium (II) catalyst was developed and well characterized. The efficiency of the supported Pd(II) catalytic material was checked for double carbonylation reaction of 2° amines and aryl iodides to their corresponding α-ketoamides under high pressure reaction conditions. The reaction was carried out in 60 psi carbon monoxide pressure. An extensive variety of aryl iodides in combination with 2° amines in presence of carbon monoxide can produce the respective α-ketoamides with superb chemoselectivity. Effect of solvents, bases, time and amount of catalyst for the production of α-ketoamides were reported. This supported Pd(II)complex was highly catalytically active and recyclable. The developed catalytic material was regenerated by filtration. It could be recycled further six times with no such profound loss in its activity.

Stabilized Cu2O nanoparticles on rGO highly catalyzed direct oxidative coupling synthesis of Α-ketoamides with molecular oxygen

In this study, a green, efficient, recyclable Cu2O nanoparticles on reduced graphene oxide (Cu2O-NPs@rGO) carbon-based composite catalyst was synthesized by facile one-pot hydrothermal method. And Cu2O-NPs@rGO catalyst was

Aerobic oxidative amidation of alkynes using titanium oxide encapsulated cuprous iodide nanoparticles (CuI@TiO2)

A catalyst consisting of titanium oxide encapsulated cuprous iodide nanoparticles was prepared via a sol-gel method using inexpensive raw materials and was harnessed successfully in the oxidative amidation of alkynes via an environmentally benign and sustainable protocol. The mechanism of action of this transformation was thoroughly discussed. The robustness of the catalyst was elucidated by the synthesis of diverse analogues of α-ketoarylamide from a variety of electron rich and poor substrates via a simple procedure in moderate to high yields, with no generation of toxic by-products, in good recyclability up to five cycles, under solvent free and aerobic conditions. The chemical nature, morphology and loading of the CuI@TiO2 nanocatalyst were investigated by TEM, SEM, XPS, EDX, powder XRD, BET, TGA and ICP-MS.

Solvent-free one-pot oxidation of ethylarenes for the preparation of α-ketoamides under mild conditions

Here we developed a highly efficient solvent-free, one-pot procedure for synthesizing α-ketoamides from ethylarenes and amines, by oxidizing a C-H bond sp3 center. A copper catalyst was employed, and the reactions proceeded smoothly at ambient temperatures. Most of the tested ethylarenes and amines were successfully converted to their corresponding α-ketoamides in moderate to excellent yields of up to 93% with three equivalents of the oxidant tert-butyl hydroperoxide.

Metal free one-pot synthesis of α-ketoamides from terminal alkenes

A practical approach towards the synthesis of α-ketoamides from readily available terminal alkenes (styrenes) has been developed. Use of inexpensive I2/2-iodoxybenzoic acid (IBX) in dimethyl sulphoxide (DMSO) as an oxidant under metal free one-pot conditions makes this methodology versatile.

Metal free synthesis of α-keto amides from 2-hydroxy acetophenones through domino alcohol oxidation-oxidative amidation reaction

An efficient method for the synthesis of α-keto amides using 2-iodoxybenzoic acid (IBX) promoted domino alcohol oxidation and oxidative amidation reaction sequence between 2-oxoalcohols and amines under metal-free conditions is developed. In this protocol, IBX is used as an oxidizing agent to synthesize the α-keto amides, which makes this methodology highly efficient, practical, and environmentally benign.

Copper-catalyzed one-pot synthesis of α-ketoamides from 1-arylethanols

A copper-catalyzed one-pot strategy for the synthesis of α-ketoamides from 1-arylethanols is described. This triple oxidation of 1-arylethanols involves alcohol oxidation, sp3 C-H oxidation, and oxidative amidation with amines. The protocol is highly efficient, delivering α-ketoamides in good to excellent yields.