18931-83-4Relevant academic research and scientific papers
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.
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.
Imidazolium Salt Catalyzed para -Selective Halogenation of Electron-Rich Arenes
Chen, Jie,Xiong, Xiaoyu,Chen, Zenghua,Huang, Jianhui
supporting information, p. 2831 - 2834 (2015/12/18)
A highly para-selective halogenation of arenes bearing coordinating groups in the presence of a dimidazolium salt as a catalyst is reported. A series of electron-rich p-haloarenes were prepared in good yields and good to excellent selectivities. We also propose a plausible mechanism for the catalytic reaction.
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
Solvent-free aromatic C-H functionalisation/halogenation reactions
Bedford, Robin B.,Engelhart, Jens U.,Haddow, Mairi F.,Mitchell, Charlotte J.,Webster, Ruth L.
experimental part, p. 10464 - 10472 (2011/01/05)
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.
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 (2007/10/04)
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
Investigations of Steric and Electronic Factors Influencing the Cyclopalladation of meta-Toluidine Analogues
Mossi, Waldo,Klaus, Alfred J.,Rys, Paul
, p. 2531 - 2537 (2007/10/02)
The cyclopalladation of two different types of aniline derivatives is described: the acetylated anilines N-(3-methylphenyl)acetamide (2a), 3-(acetylamino)-4-chlorobenzoic acid (2c), and N-(2-chlorophenyl)acetamide (2d) are cyclometalated easily with palladium(II) acetate and trifluoroacetic acid to yield the corresponding complexes 4a, 4c, and 4d, respectively, whereas the acetylated meta-toluidine N-(2-chloro-5-methylphenyl)acetamide (2b) cannot be metalated at the only accessible site between the acetylamino and the methyl group.This aromatic C-H bond can be activated, however, with the second type of meta-toluidine derivatives: the 2-chloro-5,N-dimethyl-N-nitrosoaniline (3b) readily undergoes cyclopalladation to yield the corresponding Pd(II) complex di-μ-trifluoroacetato-bisdipalladium(II) (5b) containing a five-membered palladacylce with coordination of Pd(II) at the nitroso N-atom, which is established by 15N-NMR spectroscopy.
