128592-62-1Relevant academic research and scientific papers
Cu-Catalyzed aerobic oxidative cleavage of C(sp3)–C(sp3) bond: Synthesis of α-ketoamides
Fang, Zheng,Guo, Kai,Liu, Chengkou,Yang, Man,Zhang, Jingming
supporting information, (2020/11/02)
A novel synthesis of α-ketoamides from Cu-catalyzed aerobic oxidative C(sp3)–C(sp3) bond cleavage of hydrocinnamaldehydes has been developed. Readily available and environmentally benign oxygen is used as the oxidant. This reaction avoids the use of noble metal catalysts or specialized oxidants, and chemoselectively yields α-ketoamide. Moreover, based on various control experiments, a reasonable mechanism is proposed.
POP-Pd(ii) catalyzed easy and safe: In situ carbonylation towards the synthesis of α-ketoamides from secondary cyclic amines utilizing CHCl3 as a carbon monoxide surrogate
Islam, Sk Safikul,Riyajuddin, Sk,Molla, Rostam Ali,Yasmin, Nasima,Ghosh, Kaushik,Islam, Sk. Manirul
, p. 1979 - 1987 (2020/02/13)
A novel complex catalyst, POP-palladium(ii), has been synthesized. The developed catalyst has been characterized by XRD, EDX, scanning electron microscopy (FE-SEM), HR-TEM, FTIR spectroscopy, UV-vis spectroscopy, TGA and BET isotherm analysis. The reactiv
C-H/C-C Functionalization Approach to N-Fused Heterocycles from Saturated Azacycles
Ham, Jin Su,Park, Bohyun,Son, Mina,Roque, Jose B.,Jurczyk, Justin,Yeung, Charles S.,Baik, Mu-Hyun,Sarpong, Richmond
supporting information, p. 13041 - 13050 (2020/09/01)
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
Sharma, Anup Kumar,Jaiswal, Anjali,Singh, Krishna Nand
supporting information, p. 9348 - 9351 (2019/11/11)
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.
Room temperature copper-catalyzed oxidative amidation of terminal alkynes for the synthesis of α-ketoamides using: O -benzoyl hydroxylamines as aminating reagent and oxidant
Shen, Guodong,Zhao, Lingyu,Wang, Yichen,Zhang, Tongxin
, p. 78307 - 78310 (2016/09/09)
A novel and convenient copper-catalyzed oxidative amidation for the synthesis of α-ketoamides has been successfully developed, which uses easily available O-benzoyl hydroxylamines as aminating reagent and oxidant. The reaction proceeds smoothly at room temperature and is compatible with a range of substrates to give the desired products in moderate to good yields.
I2-promoted aerobic oxidative coupling of acetophenes with amines under metal-free conditions: Facile access to α-ketoamides
Guo, Shiyu,Fang, Zheng,Yang, Zhao,Liu, Chengkou,Dai, Zhongxue,Zhao, Lihuan,Guo, Kai
, p. 1503 - 1507 (2016/01/16)
A novel and efficient I2-promoted oxidative coupling of acetophenes with amines to α-ketoamides is presented, which employs O2 as an environmentally friendly oxidant under metal-free conditions. Based on a series of control experimen
Cu(i)-Functionalized SBA-16: An efficient catalyst for the synthesis of α-ketoamides under moderate conditions
Zhang, Xueyao,Yang, Honglei,Huo, Yong,Li, Jing,Ma, Jianxin,Ma, Jiantai
, p. 8972 - 8983 (2016/06/09)
An efficient catalyst based on the cage-like mesoporous material SBA-16 as the support and Cu(i) as active sites has been successfully prepared. The catalyst demonstrated high catalytic activity (up to 88%) in the direct oxidative synthesis of α-ketoamides between acetophenone and piperidine, employing O2 from open air as the oxidant without other additives. A heterogeneous catalyst was applied in this reaction for the first time, and the catalyst could be easily separated from the reaction system by filtration and reused several times without a significant loss of activity.
Metal free synthesis of α-keto amides from 2-hydroxy acetophenones through domino alcohol oxidation-oxidative amidation reaction
Kotha, Surya Srinivas,Sekar, Govindasamy
supporting information, p. 6323 - 6326 (2015/11/11)
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
Sharma, Nidhi,Kotha, Surya Srinivas,Lahiri, Nabajit,Sekar, Govindasamy
, p. 726 - 736 (2015/04/14)
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.
Mild gold-catalyzed aerobic dehydrogenative coupling of amines and phenylglyoxal derivatives
Shao, Ying,Wu, Zhuhong,Miao, Chunbao,Liu, Li
, p. 60 - 64 (2014/07/07)
A simple and efficient gold-catalyzed coupling of secondary amine with phenylglyoxal derivatives has been developed, which provides a practical synthetic strategy for the synthesis of substituted α-ketoamides under mild reaction conditions.
