- A Visible Light-Mediated Regioselective Halogenation of Anilides and Quinolines by Using a Heterogeneous Cu-MnO Catalyst
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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.
- Singh, Harshvardhan,Sen, Chiranjit,Sahoo, Tapan,Ghosh, Subhash Chandra
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p. 4748 - 4753
(2018/09/06)
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- Cobalt(II)-catalyzed regioselective C-H halogenation of anilides
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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.
- Li, Ze-lin,Sun, Kang-kang,Cai, Chun
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supporting information
p. 5433 - 5440
(2018/08/12)
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- Story of an Age-Old Reagent: An Electrophilic Chlorination of Arenes and Heterocycles by 1-Chloro-1,2-benziodoxol-3-one
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By the use of 1-chloro-1,2-benziodoxol-3-one, an age-old reagent, the practical and efficient chlorination method is achieved. This hypervalent iodine reagent is amenable not only to the chlorination of nitrogen-containing heterocycles but also to selected classes of arenes, BODIPY dyes, and pharmaceuticals. In addition, the advantages, such as easy preparation and recyclable, air- and moisture-stable, in combination with the success in a gram-scale experiment grant this reagent great potential for industrial application.
- Wang, Mengzhou,Zhang, Yanyan,Wang, Tao,Wang, Chao,Xue, Dong,Xiao, Jianliang
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supporting information
p. 1976 - 1979
(2016/06/01)
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- Direct acetoxylation and etherification of anilides using phenyliodine bis(trifluoroacetate)
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Treatment of various anilides with 1.5 equiv. of phenyliodine bis(trifluoroacetate) (PIFA) and 1.0 equiv. of BF3·OEt 2 in AcOH at room temperature afforded the corresponding para-acetoxylated products with high regioselectivity. In addition, this reaction could be expanded to the etherification of anilides. In the presence of 2.0 equiv. of PIFA and 2.0 equiv. of BF3·OEt2, the reaction of anilides with alcohols provided the corresponding para-etherified products in good yields. The Royal Society of Chemistry 2011.
- Liu, Huan,Wang, Xuemin,Gu, Yonghong
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experimental part
p. 1614 - 1620
(2011/04/22)
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- Palladium-catalyzed C-H aminations of anilides with N - fluorobenzenesulfonimide
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The first amide-directed, palladium-catalyzed, intermolecular, highly selective C-H aminations with the non-nitrene-based nitrogen source N-fluorobenzenesulfonimide have been developed. This methodology might provide a new pathway for directed metal-catalyzed aromatic C-H amination.
- Sun, Kai,Li, Yan,Xiong, Tao,Zhang, Jingping,Zhang, Qian
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supporting information; experimental part
p. 1694 - 1697
(2011/04/17)
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- Solvent-free aromatic C-H functionalisation/halogenation reactions
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The solvent-free, palladium-catalysed reaction of anilides with CuCl 2 in the presence or absence of copper acetate yields ortho-chlorinated anilides in good to excellent yields, even on a large scale (100 mmol). By contrast, the equivalent reactions with copper bromide, either solvent free or in 1,2-dichloroethane, in the presence or absence of palladium, under air or inert conditions, gave the products of simple electrophilic bromination. Mechanistic studies highlighted the involvement of palladacyclic intermediates, one of which was characterised crystallographically, which undergo subsequent reaction with copper(ii) chloride to yield the chlorinated anilide products.
- Bedford, Robin B.,Engelhart, Jens U.,Haddow, Mairi F.,Mitchell, Charlotte J.,Webster, Ruth L.
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supporting information; experimental part
p. 10464 - 10472
(2011/01/05)
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- Highly selective C-H functionalization/halogenation of acetanilide
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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
- Wan, Xiaobing,Ma, Zhongxun,Li, Bijie,Zhang, Keya,Cao, Shaokui,Zhang, Shiwei,Shi, Zhangjie
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p. 7416 - 7417
(2007/10/04)
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- Imidazopyridines for the treatment of neurological disorders
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Corticotropin releasing factor (CRF) antagonists of formula (I): and their use in treating psychiatric disorders and neurological diseases, anxiety-related disorders, post-traumatic stress disorder, supranuclear palsy and feeding disorders as well as treatment of immunological, cardiovascular or heart-related diseases and colonic hypersensitivity associated with psychopathological disturbance and stress in mammals.
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- Imidazopyrimidines and imidazopyridines for the treatment of neurological disorders
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Corticotropin releasing factor (CRF) antagonists of formula (I): and their use in treating psychiatric disorders and neurological diseases, anxiety-related disorders, post-traumatic stress disorder, supranuclear palsy and feeding disorders as well as treatment of immunological, cardiovascular or heart-related diseases and colonic hypersensitivity associated with psychopathological disturbance and stress in mammals.
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- Oxidative chlorination of acetanilides with hydrogen chloride/m-chloroperbenzoic acid/N,N-dimethylformamide system
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The reaction of acetanilides with relevant amounts of HCl and m-chloroperbenzoic acid in DMF at room temperature gave the desired chloro-substituted acetanilides in good yields.
- Chung,Kim,Kim,Ryu
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p. 1917 - 1922
(2007/10/02)
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