1020-39-9Relevant articles and documents
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Tokura et al.
, p. 3135 (1957)
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Highly selective C-H functionalization/halogenation of acetanilide
Wan, Xiaobing,Ma, Zhongxun,Li, Bijie,Zhang, Keya,Cao, Shaokui,Zhang, Shiwei,Shi, Zhangjie
, p. 7416 - 7417 (2006)
Highly regioselective C-H functionalization/halogenation of acetanilides to produce ortho-haloacetanilides was catalyzed by Pd(OAc)2 and Cu(OAc)2 with CuX2 as the halogen source. Copyright
TBHP-mediated highly efficient dehydrogenative cross-oxidative coupling of methylarenes with acetanilides
Chen, Cui,Liu, Weibing,Zhou, Peng
, p. 2250 - 2255 (2016)
A TBHP-mediated dehydrogenative cross-oxidative-coupling approach has been developed for the synthesis of N-arylbenzamides from methylarenes and acetanilides. This cross-coupling method is free of transition metal catalysts and ligands, and no extra organic solvents are required, which make it an useful and attractive strategy for the straightforward construction of C-N bonds. Besides, this conversion is an important complement to the conventional C-N forming strategies.
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Porter,Wilcox
, p. 2688 (1934)
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Halogenase-Inspired Oxidative Chlorination Using Flavin Photocatalysis
Hering, Thea,Mühldorf, Bernd,Wolf, Robert,K?nig, Burkhard
, p. 5342 - 5345 (2016)
Chlorine gas or electropositive chlorine reagents are used to prepare chlorinated aromatic compounds, which are found in pharmaceuticals, agrochemicals, and polymers, and serve as synthetic precursors for metal-catalyzed cross-couplings. Nature chlorinates with chloride anions, FAD-dependent halogenases, and O2 as the oxidant. A photocatalytic oxidative chlorination is described based on the organic dye riboflavin tetraacetate mimicking the enzymatic process. The chemical process allows within the suitable arene redox potential window a broader substrate scope compared to the specific activation in the enzymatic binding pocket. Chlorination of arenes with chloride anions: The photochemical analogue of the enzymatic chlorination of Flavin-adenine dinucleotide (FAD)-dependent halogenases is possible in the presence of riboflavin, air, acetic acid, and blue light (see scheme; RFT=riboflavin tetraacetate).
Migration of the Hydroxyl Group of N-Hydroxy-N-phenylamides to the Phenyl Group with Tertiary Phosphines and Tetrachloromethane. A Novel Transhydroxylation Reaction
Kikugawa, Yasuo,Mitsui, Kimiyo
, p. 1369 - 1372 (1993)
The hydroxyl group of N-hydroxyl-N-phenylamides rearranges mainly to the ortho position of the N-phenyl ring by the system (n-Bu)3P-CCl4-CH3CN; use of less than a stoichiometric amount of (n-Bu)3P is effective for this reaction.
Pd-Catalyzed Oxidation of Aldimines to Amides
Gao, Shanshan,Ma, Yaorui,Chen, Weidong,Luo, Junfei
, p. 2191 - 2194 (2018)
Methods for the synthesis of amides via the direct oxidation of imines are rarely reported. Here we report an efficient method for Pd-catalyzed oxidation of imines to amide derivatives by the use of cheap aqueous tert -butyl hydroperoxide as an oxidant through a Wacker-type reaction. This method is practically convenient and displays high functional group tolerance, allowing a variety of imines to transform into the corresponding amide derivatives in moderate to good yields.
Efficient cobalt-catalyzed C-N cross-coupling reaction between benzamide and aryl iodide in water
Tan, Bryan Yong-Hao,Teo, Yong-Chua
, p. 7478 - 7481 (2014)
A practical and efficient strategy for the N-arylation of benzamide catalysed by a Co(C2O4)·2H2O/dmeda system in water is reported. Under the optimized conditions, a wide variety of N-arylated products were obtained in good yields (up to 92%) using substituted aryl iodides.
Copper(I) iodide–catalyzed amidation of phenylboronic acids/aryl bromides using 4-dimethylaminopyridine as ligand
Alapati, Mohan Lakshmi Punna Rao,Abburu, Sridhar Rao,Mutyala, Krishnaji Rao,Mukkamala, Saratchandra Babu
, p. 1242 - 1248 (2016)
An efficient one-pot synthesis of N-arylbenzamide is described via reaction of phenylboronic acid/aryl bromide with benzamide in the presence of CuI (5?mol%) as catalyst, 4-dimethylaminopyridine (20?mol%) as the ligand, and Cs2CO3(2?mmol) as the base. This protocol was applied to synthesize a small library of N-arylbenzamide in high yields.
Ligand-free Pd(0)/SiO2-catalyzed aminocarbonylation of aryl iodides to amides under atmospheric CO pressure
Hu, Qinhua,Wang, Lele,Wang, Chen,Wu, Yubin,Ding, Zhengxin,Yuan, Rusheng
, p. 37200 - 37207 (2017)
An efficient and facile route for CO-based carbonylation of aryl iodides with amines to synthesize amides has been established by using SiO2 supported Pd(0) as the catalyst in a mild basic environment (K2CO3). This ligand-free heterogeneous reaction model can afford amide products in good to excellent yields (up to 99%) under atmospheric CO pressure and moderate temperature. The supported catalyst also displayed a broad substrate scope, good functional group tolerance and good recyclability. These features render the as-provided carbonylation approach sustainable and applicable in organic synthesis.
Brine-mediated efficient benzoylation of primary amines and amino acids
Chattopadhyay, Gautam,Chakraborty, Suchandra,Saha, Chandan
, p. 4068 - 4075 (2008)
Benzoylation of primary amines and amino acids is efficiently carried out in a brine solution using a stoichiometric amount of benzoyl chloride followed by trituration with aqueous saturated bicarbonate solution. Copyright Taylor & Francis Group, LLC.
Novel and efficient heterogeneous polymer supported copper catalyst for synthesis of 2-substituted Benzoxazoles from 2-Haloanilides
Saranya, Thachora Venu,Sruthi, Pambingal Rajan,Raj, Veena,Anas, Saithalavi
supporting information, (2021/02/27)
A novel polymer supported copper complex is prepared by the immobilization of copper iodide on chemically modified polyacrylonitrile and its application in heterogeneous catalysis is described. The catalyst was prepared by easy method via synthetic modification of Polyacrylonitrile (PAN) using ethylene diamine followed by the complexation with CuI. After characterization, this complex was explored as a green and efficient heterogeneous catalyst for the synthesis of 2-benzoxazoles from 2-haloanilides. The reaction was performed without adding additional ligand and the catalyst shows activity over a broad range of substrates with quantitative product yields. The catalyst was easily recovered by simple filtration and reused successfully for further cycle.
Synthesis of 2-Amino-1,3-dienes from Propargyl Carbonates via Palladium-Catalyzed Carbon-Nitrogen Bond Formation
O'Broin, Calvin Q.,Guiry, Patrick J.
supporting information, p. 879 - 883 (2020/02/04)
A catalytic method to synthesize 1,3,-dienes from propargylic precursors is reported. This palladium-catalyzed carbon-nitrogen bond-forming reaction furnishes 2-amino-1,3-dienes in excellent yields (up to 98%) and shows a broad tolerance to functional group diversity. The reaction has been demonstrated for over 30 amine substrates, including anilines and indoles, and proceeds under mild neutral conditions. The resulting 1,3-dienes are of great synthetic interest because of their further reaction potential.
