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Relevant academic research and scientific papers

Palladium Catalyzed Cascade Azidation/Carbonylation of Aryl Halides with Sodium Azide for the Synthesis of Amides

Amide synthesis is one of the most important transformations in organic chemistry due to their ubiquitous presence in our daily life. In this communication, a palladium catalyzed cascade azidation/carbonylation of aryl halides for the synthesis of amides was developed. Both iodo- and bromobenzene derivatives were transformed to the corresponding amides using PdCl2/xantphos as the catalyst system and sodium azide as the nitrogen-source. The reaction proceeds via a cascade azidation/carbonylation process. A range of alkyl and halogen substituted amides were prepared in moderate to good yields.

Supported-Pd catalyzed tandem approach for N-arylbenzamides synthesis

Aryl iodides as dual arylating agent for C-terminal from oxalic acid [(CO2H)2] and N-terminal from sodium azide (NaN3) for N-aryl benzamides (Ar-CO-NH-Ar) synthesis is a rare invention which has been attempted successfully under this study. A single step tandem approach for the synthesis of N-aryl benzamides has been developed through bifunctional transformation of aryl iodides with in-situ CO from (CO2H)2 and NaN3 following two different pathways of carbonylation and azidation. The polystyrene supported palladium (Pd@PS) catalyst was found to be well compatible to perform the domino-reaction in a double layer vial (DLV) system under base, ligand and additive-free conditions. Moreover, the same approach was further extended with aryl azides for unsymmetric N-aryl benzamides (Ar-CO-NH-Ar') synthesis. Furthermore, the DFT studies were also performed to support the proposed mechanism.

Vilsmeier-Haack reagent mediated synthetic transformations with an immobilized iridium complex photoredox catalyst

An immobilized iridium complex photocatalyst Ir(ppy)2(PDVB-py) was synthesized by immobilization of the iridium complex onto the nanoporous vinylpyridine-divinylbenzene copolymer (PDVB-py). Its application for the synthesis of amides, nitriles, and anhydrides was reported via reactions under the action of the visible-light-driven in situ generated Vilsmeier-Haack reagent from CBr4 in DMF. The results showed that this heterogeneous photocatalyst has extremely high activity and excellent stability to be recycled five times.

Microdroplets as Microreactors for Fast Synthesis of Ketoximes and Amides

The formation of amide bonds is one of the most valuable transformations in organic synthesis. Beckmann rearrangement is a well-known method for producing secondary amides from ketoximes. This study demonstrates the rapid synthesis of ketoximes and amides in microdroplets. Many factors are found to affect the yield, such as microdroplet generation devices, temperature, catalysts, and concentrations of reactants. In particular, the temperature has a great influence on the synthesis of amide, which is demonstrated by a sharp ascendance to the yield when the temperature was increased to 45 °C. The best amide yield (93.3%) can be obtained by using coaxial flowing devices, a sulfonyl chloride compound as a catalyst, and heating to 55 °C in microdroplets. The yields can reach 78.7-91.3% for benzoylaniline and 87.2-93.4% for benzophenone oximes in several seconds in microdroplets compared to 10.1-66.1% and 82.5-93.3% in several hours in the bulk phase. Apart from the dramatically decreased reaction time and enhanced reaction yields, the microdroplet synthesis is also free of severe reaction environments (anhydrous and anaerobic conditions). In addition, the synthesis in microdroplets also saves reactants and solvents and reduces the waste amounts. All of these merits indicate that the microdroplet synthesis is a high-efficiency green methodology.

o-Phthalic Anhydride/Zn(OTf)2 co-catalyzed Beckmann rearrangement under mild conditions

o-Phthalic anhydride/Zn(OTf)2 co-catalyzed Beckmann rearrangement was developed, producing the corresponding amide in up to 99% yield with acid-sensitive functionalities tolerated well, and the scale of the reaction could be enlarged to 77 mmol and the excellent yield was maintained. A successive procedure was developed. Moreover, the reaction was carried out at rt under nearly neutral conditions, and the workup was concise. These features illustrated the potential of the protocol in amide synthesis.

Beckmann rearrangement of ketoxime catalyzed by N-methyl-imidazolium hydrosulfate

Beckmann rearrangement of ketoxime catalyzed by acidic ionic liquid-N-methyl-imidazolium hydrosulfate was studied. Rearrangement of benzophenone oxime gave the desirable product with 45% yield at 90 ?C. When co-catalyst P2O5 was added, the yield could be improved to 91%. The catalyst could be reused three cycles with the same efficiency. Finally, reactions of other ketoximes were also investigated.

Hypervalent Iodine-Mediated Oxidative Rearrangement of N-H Ketimines: An Umpolung Approach to Amides

An umpolung approach to amides via hypervalent iodine-mediated oxidative rearrangement of N-H ketimines under mild reaction conditions is described. This strategy provides target amides with excellent selectivity in good yields. In addition, preliminary m

Lewis acid-assisted N-fluorobenzenesulfonimide-based electrophilic fluorine catalysis in Beckmann rearrangement

A microwave-assisted N-fluorobenzenesulfonimide (NFSI)/Lewis acid-catalyzed Beckmann rearrangement was developed. The remarkable promotion to the electrophilicity of NFSI by Lewis acids was illustrated utilizing a series of readily available oxime substrates. The action model between NFSI and Lewis acids was probed by control experiments and theoretical calculations.

Ligand-Free Copper-Manganese Spinel Oxide-Catalyzed Tandem One-Pot C–H Amidation and N-Arylation of Benzylamines: A Facile Access to 2-Arylquinazolin-4(3H)-ones

An efficient ligand-free copper-manganese (Cu-Mn) spinel oxide-catalyzed direct tandem C?H oxygenation and N-arylation of benzylamines has been developed. The method has been utilized for the synthesis of medicinally important 2-arylquinazolin-4(3H)-ones. Salient features of this method include recyclable catalyst, no ligand, excellent product yields, shorter reaction times and a broad substrate scope. (Figure presented.).

An Iron-Catalyzed Direct Approach to Amides from Benzyl Azides via C-C Bond Cleavage

A novel iron-catalyzed transformation of benzyl azides to give the corresponding amides via C-C bond cleavage under mild reaction conditions is developed. This method provides a new synthetic tool for the construction of amides and the opportunity to accomplish C-C functionalization under mild conditions.