23373-04-8Relevant articles and documents
Nickel(II)- And Silver(I)-Catalyzed C-H Bond Halogenation of Anilides and Carbamates
Kianmehr, Ebrahim,Afaridoun, Hadi
, p. 1513 - 1523 (2020/12/14)
ortho -C-H bond halogenation of anilides and N -aryl carbamates using easily available N -halosuccinimides (NXS) as the active halogenation reagent in the presence of nickel or silver catalyst has been developed. This method provides a new approach to 2-haloanilides and carbamates, which may serve as starting materials for the synthesis of pharmaceutically and biologically active compounds.
A Visible Light-Mediated Regioselective Halogenation of Anilides and Quinolines by Using a Heterogeneous Cu-MnO Catalyst
Singh, Harshvardhan,Sen, Chiranjit,Sahoo, Tapan,Ghosh, Subhash Chandra
, p. 4748 - 4753 (2018/09/06)
A simple and practical heterogeneous Cu-MnO catalyzed regioselective halogenation of anilides and quinolines under irradiation with household 40 W incandescent lamp was developed. This method uses a recyclable Cu-MnO catalyst, acetonitrile as an industrially friendly solvent, and economic N-halo succinimides as a halogenating source. The reaction is scalable and well tolerated with a broad range of functional groups.
Cobalt(II)-catalyzed regioselective C-H halogenation of anilides
Li, Ze-lin,Sun, Kang-kang,Cai, Chun
supporting information, p. 5433 - 5440 (2018/08/12)
A cobalt-catalyzed regioselective C-H halogenation methodology is reported herein. The highlight of this work is the highly selective C-H functionalization of anilides, which results in high-yielding, versatile, and practical halogenated products. Thereby, brominations, chlorinations and iodinations of many electron-rich and electron-deficient anilides were achieved in a highly selective fashion. Mechanistic studies with respect to the pathway of the reaction are also described.
A para-C–H Functionalization of Aniline Derivatives via In situ Generated Bulky Hypervalent Iodinium Reagents
Tian, Chao,Yao, Xu,Ji, Weizhe,Wang, Qian,An, Guanghui,Li, Guangming
supporting information, p. 5972 - 5979 (2018/11/23)
A practical para-C-H functionalization of aniline derivatives has been developed using an in situ generated bulky hypervalent iodinium reagent. Para-iodo, bromo, chloro, nitro, trifluormethyl aniline derivatives can be obtained efficiently, in many cases in 10 min in a transition metal-free manner. Medicinal chemicals or intermediates can be purified without column chromatography or recrystallization, which significantly reduces the waste and simplifies the work-up process.
Monoprotected l-Amino Acid (l-MPAA), Accelerated Bromination, Chlorination, and Iodination of C(sp2)?H Bonds by Iridium(III) Catalysis
Kathiravan, Subban,Nicholls, Ian A.
supporting information, p. 7031 - 7036 (2017/05/29)
Halogenated arenes are important structural motifs commonly found in biologically active molecules and used for a variety of transformations in organic synthesis. Herein, we report the mono-protected l-amino acid (l-MPAA) accelerated iridium(III)-catalyzed halogenation of (hetero)anilides at room temperature. This reaction constitutes the first example of an iridium(III)/l-MPAA-catalyzed general halogenation of (hetero)arenes through C(sp2)?H activation. Furthermore, we demonstrate the potential utility of our method through its use in the synthesis of a quinolone derivative.
Synthesis of 2-methylbenzoxazoles directly from: N -phenylacetamides catalyzed by palladium acetate
Wang, Biying,Jiang, Chengfei,Qian, Jiasheng,Zhang, Shuwei,Jia, Xiaodong,Yuan, Yu
, p. 101 - 107 (2017/12/27)
A method to synthesize 2-methylbenzoxazoles directly from N-phenylacetamides catalyzed by Pd(OAc)2 in the presence of K2S2O8 and TfOH has been developed. The desired products were obtained in moderate to excellent yields. This approach provides a facile procedure to prepare benzoxazoles with available substrates. It is found that TfOH is the key factor for this cyclization reaction. A plausible mechanism of the reaction is proposed according to the control reactions and the literature.
Regioselective and efficient bromination of anilides on water using HBr and Selectfluor
Liang, Deqiang,Li, Xiangguang,Wang, Chaowu,Dong, Qishan,Wang, Baoling,Wang, Hai
supporting information, p. 5390 - 5394 (2016/11/11)
A metal-, additive-, and Br2-free highly regioselective bromination of anilides using HBr and Selectfluor is presented. This reaction proceeded under mild conditions with high efficiency and good functional group tolerance, and water served as the solvent. In general, with substrates bearing no para-substituent, para-mono-bromination occurred exclusively, while ortho-mono-brominated anilides were the only products when para-positions were blocked. The incorporation of a stronger orienting group might result in a reversed regioselectivity, and the reaction was sensitive to steric hindrance.
Bromination of arenes using I2O5-KBr in water
Hou, Jieping,Li, Zejiang,Jia, Xiao-Dong,Liu, Zhong-Quan
supporting information, p. 181 - 187 (2013/12/04)
An efficient and environmentally benign bromination of various aromatic compounds using aN aqueous I2O5-KBr system at room temperature has been developed in this work. A series of aromatic compounds such as acetophenones, benzaldehydes, benzoic acids, anilines, amides, and aminopyridine have been successfully brominated in excellent regioselectivities and good yields under the typical reaction conditions. The features of KBr as brominating reagent, water as solvent, and mild conditions make this system an attractive synthetic procedure. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
Air oxidation of N-cyclopropylanilines
Blackburn, Anthony,Bowles, Daniel M.,Curran, Timothy T.,Kim, Hui
, p. 1855 - 1863 (2012/04/10)
Air oxidation of N-cyclopropylanilines was shown to occur under either ambient conditions or accelerated conditions (warming or shining light) in an open container. A subsequent fragmentation resulted in formation of the corresponding acetamide. While potential mechanisms have been previously proposed, simple aerobic oxidation to β-hydroxy-propionamides in the absence of a radical promoter has not been previously reported. Copyright Taylor & Francis Group, LLC.
Mild C - H halogenation of anilides and the isolation of an unusual palladium(I)-palladium(II) species
Bedford, Robin B.,Haddow, Mairi F.,Mitchell, Charlotte J.,Webster, Ruth L.
supporting information; experimental part, p. 5524 - 5527 (2011/07/31)
Reducing the load: A facile palladium-catalyzed ortho-selective bromination and chlorination of anilides occurs under aerobic conditions at room temperature when N-halosuccinimides (NXS) are used in the presence of p-toluenesulfonic acid (PTSA). The orthopalladated PTSA complex is not only catalytically competent but also undergoes a reductive process to yield an unusual PdI-PdII tetramer (see structure; Pdgreen, Ored, Syellow, Cgray). Copyright
