3034-34-2Relevant articles and documents
Ring Opening/Site Selective Cleavage in N-Acyl Glutarimide to Synthesize Primary Amides
Govindan, Karthick,Lin, Wei-Yu
supporting information, p. 1600 - 1605 (2021/03/03)
A LiOH-promoted hydrolysis selective C-N cleavage of twisted N-acyl glutarimide for the synthesis of primary amides under mild conditions has been developed. The reaction is triggered by a ring opening of glutarimide followed by C-N cleavage to afford primary amides using 2 equiv of LiOH as the base at room temperature. The efficacy of the reactions was considered and administrated for various aryl and alkyl substituents in good yield with high selectivity. Moreover, gram-scale synthesis of primary amides using a continuous flow method was achieved. It is noted that our new methodology can apply under both batch and flow conditions for synthetic and industrial applications.
Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(sp3)?H Bonds**
Murugesan, Kathiravan,Donabauer, Karsten,K?nig, Burkhard
supporting information, p. 2439 - 2445 (2020/12/07)
The metal-free activation of C(sp3)?H bonds to value-added products is of paramount importance in organic synthesis. We report the use of the commercially available organic dye 2,4,6-triphenylpyrylium tetrafluoroborate (TPP) for the conversion of methylarenes to the corresponding aryl nitriles via a photocatalytic process. Applying this methodology, a variety of cyanobenzenes have been synthesized in good to excellent yield under metal- and cyanide-free conditions. We demonstrate the scope of the method with over 50 examples including late-stage functionalization of drug molecules (celecoxib) and complex structures such as l-menthol, amino acids, and cholesterol derivatives. Furthermore, the presented synthetic protocol is applicable for gram-scale reactions. In addition to methylarenes, selected examples for the cyanation of aldehydes, alcohols and oximes are demonstrated as well. Detailed mechanistic investigations have been carried out using time-resolved luminescence quenching studies, control experiments, and NMR spectroscopy as well as kinetic studies, all supporting the proposed catalytic cycle.
Nano-construction of CuO nanorods decorated with g-C3N4 nanosheets (CuO/g-C3N4-NS) as a superb colloidal nanocatalyst for liquid phase C[sbnd]H conversion of aldehydes to amides
Mohammadi, Robabeh,Gholipour, Behnam,Alamgholiloo, Hassan,Rostamnia, Sadegh,Mohtasham, Hamed,Zonouzi, Afsaneh,Ramakrishna, Seeram,Shokouhimehr, Mohammadreza
, (2021/04/27)
Herein, we describe an intelligent strategy to fabricate nanosheets of graphitic carbon nitride (g-C3N4) decorated with nanorods copper oxide (CuO NRs). Then, the catalytic activity of CuONRs/g-C3N4-NS was developed for the synthesis of primary amides in water. The morphology of CuO and its synergetics effect with nanosheets g-C3N4 a major role in the yield of products. Furthermore, hydroxylamine hydrochloride (NH2OH·HCl) due to availability and affordability was used as a suitable substitute for ammonia source. The findings demonstrate that this layer nanostructure is a superb catalyst for converting various derivatives of aldehyde to their corresponding amides. The current protocol can be useful criterion in the synthesis and stabilization of metal oxides and provides new insight in organic transformation.