164322-25-2Relevant articles and documents
Straightforward Synthesis of α-Chloromethylketimines Catalyzed by Gold(I). A Clean Way to Building Blocks
Asensio, Gregorio,Cárcel, María,Olmos, Andrea,Ramírez De Arellano, Carmen,Sarmiento, Jeymy T.,Varea, Teresa
, p. 3114 - 3122 (2022/03/14)
α-Chloromethylketimines have been obtained through a gold-catalyzed hydroamination of aromatic and aliphatic 1-chloroalkynes with aromatic amines by using equimolar amounts of both reagents. This procedure has allowed the preparation and spectroscopic characterization of α-chloromethylketimines for the first time with a high degree of purity, complete conversion, and atom economy. The synthetic usefulness of the methodology has been demonstrated with the preparation of β-chloroamines and indoles.
Unmasking the Hidden Carbonyl Group Using Gold(I) Catalysts and Alcohol Dehydrogenases: Design of a Thermodynamically-Driven Cascade toward Optically Active Halohydrins
Escot, Lorena,González-Granda, Sergio,Gotor-Fernández, Vicente,Lavandera, Iván
, p. 2552 - 2560 (2022/02/16)
A concurrent cascade combining the use of a gold(I) N-heterocyclic carbene (NHC) and an alcohol dehydrogenase (ADH) is disclosed for the synthesis of highly valuable enantiopure halohydrins in an aqueous medium and under mild reaction conditions. The meth
A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions
Wang, Zhihui,Wang, Lei,Wang, Zhiming,Li, Pinhua,Zhang, Yicheng
supporting information, p. 429 - 432 (2020/02/29)
A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions has been developed. In the presence of PhI(OAc)2 as promoter and under ambient conditions, the reactions of styrenes and triiodomethane undergo the transformation smoothly to deliver the corresponding α-iodoketones without additional photocatalyst in good yields under sunlight irradiation. Meanwhile, the reactions of styrenes with tribromomethane and trichloromethane generate the desired α-bromoketones and α-chloroketones in high yields by using Ru(bpy)3Cl2 as a photocatalyst under blue LED (450–455 nm) irradiation.
Mild oxidation of benzyl alcohols to benzyl aldehydes or ketones catalyzed by visible light
Cheng, Dongping,Li, Xiaonian,Ren, Shujian,Xu, Xiaoliang
supporting information, (2021/07/02)
Induced by visible light, mild oxidation condition to prepare benzyl aldehydes or ketones have been developed by using bromotrichloromethane as photochemical oxidant. This method avoids high temperature, pressure and peroxidation with only visible light as the green driving force.
Chemoselective Hydro(Chloro)pentafluorosulfanylation of Diazo Compounds with Pentafluorosulfanyl Chloride
Qing, Feng-Ling,Shou, Jia-Yi,Xu, Xiu-Hua
supporting information, p. 15271 - 15275 (2021/06/08)
Pentafluorosulfanyl chloride (SF5Cl) is the most prevalent reagent for the incorporation of SF5 group into organic compounds. However, the preparation of SF5Cl often relies on hazardous reagents and specialized apparatus. Herein, we described a safe and practical synthesis of a bench-stable and easy-to-handle solution of SF5Cl in n-hexane under gas-reagent-free conditions. The synthetic application of SF5Cl was demonstrated through the unprecedented reaction with diazo compounds. The chemoselective hydro- and chloropentafluorosulfanylations of α-diazo carbonyl compounds were developed in the presence of K3PO4 or copper catalyst, respectively. These reactions provide a direct and efficient access to various α-pentafluorosulfanyl carbonyl compounds of high value for potential applications.
Tris-(2-pyridylmethyl)amine-ligated Cu(II) 1,3-diketonate complexes: Anaerobic retro-Claisen and dehalogenation reactivity of 2-chloro-1,3-diketonate derivatives
Elsberg, Josiah G. D.,Anderson, Stephen N.,Tierney, David L.,Reinheimer, Eric W.,Berreau, Lisa M.
, p. 1712 - 1720 (2021/02/22)
We report synthetic, structural and reactivity investigations of tris-(2-pyridylmethyl)amine (TPA)-ligated Cu(ii) 1,3-diketonate complexes. These complexes exhibit anaerobic retro-Claisen type C-C bond cleavage reactivity which exceeds that found in analo
One-pot synthesis of 4-aryl-2-aminothiazoles from styrenes and thioureas promoted by tribromoisocyanuric acid
de Andrade, Vitor S.C.,de Mattos, Marcio C.S.
supporting information, (2020/07/03)
A simple and efficient one-pot protocol has been developed for the conversion of styrenes into 4-aryl-2-aminothiazoles using readily available starting materials. Tribromoisocyanuric acid was successfully used for the co-bromination and oxidation of styrenes to give phenacyl bromides, which in the presence of thioureas produced the corresponding 4-aryl-2-aminothiazoles in 48–70% yield. The protocol involves three reactions in one process: a tandem (formation of phenacyl bromides from styrenes) followed by a telescoped (conversion to thiazole) reaction.
Facile Synthesis of α-Haloketones by Aerobic Oxidation of Olefins Using KX as Nonhazardous Halogen Source
Luo, Zhibin,Meng, Yunge,Gong, Xinchi,Wu, Jie,Zhang, Yulan,Ye, Long-Wu,Zhu, Chunyin
supporting information, p. 173 - 177 (2020/01/02)
An operationally simple and safe synthesis of α-haloketones using KBr and KCl as nonhazardous halogen sources is reported. It involves an iron-catalysed reaction of alkenes with KBr/KCl using O2 as terminal oxidant under the irradiation of visible-light. This strategy avoids the risks associated with handling halo-contained electrophiles (Cl2, Br2, NCS, NBS). The process is tolerant to several functional groups, and extended to a range of substituted styrenes in up to 89% yield. A radical reaction pathway is proposed based on control experiments and spectroscopy studies.
2-Bromoanthraquinone as a highly efficient photocatalyst for the oxidation ofsec-aromatic alcohols: experimental and DFT study
Chen, Guanghui,Liao, Shengfu,Liu, Jianguo,Liu, Qiying,Ma, Longlong,Yan, Long
, p. 37014 - 37022 (2020/10/27)
Anthraquinones are recognized as high efficiency photocatalysts which can perform various redox reactions in aqueous or organic phases. We have experimentally proven that 2-BrAQ can undergo hydrogen transfer with an alpha-aromatic alcohol under light conditions, thereby efficiently oxidizing the aromatic alcohol to the corresponding product. The yield of 1-phenethanol to acetophenone can reach more than 96%. In subsequent catalyst screening experiments, it was found that the electronegativity of the substituent at the 2 position of the anthraquinone ring and the acidity of the solvent affect the photocatalytic activity of anthraquinones. After using various aromatic alcohol substrates, 2-BrAQ showed good conversion and selectivity for most aromatic alcohols, but showed C-C bond cleavage and low selectivity with non-α-position aromatic alcohols. In order to explore the mechanism of the redox reaction of 2-BrAQ in acetonitrile solution, the corresponding free radical reaction pathway was proposed and verified by density functional theory (DFT). Focusing on calculations for 2-BrAQ during the reaction and the first-step hydrogen transfer reaction between the 2-BrAQ triplet molecule and the 1-phenylethanol molecule, we recognized the changes that occurred during the reaction and thus have a deeper understanding of the redox reaction of anthraquinone compounds in organic systems.
Facile Approach to Geminal HeterodihalogenationOne-Pot Synthesis of α-Bromo-α-Chloro Ketones
Bian, Ming,Tang, Dong-Min,Zhou, Jin-Feng
, (2020/09/09)
An efficient and practical protocol for the geminal heterodihalogenation of methyl ketones by using readily available dimethyl sulfoxide and a combination of HCl and HBr is reported. Control experiments suggested that the acidity of the solution, as well as the oxidizing ability and nucleophilicity of the dimethyl sulfoxide might work cooperatively in ensuring the success of the tandem substitution. Its operational simplicity, easy accessibility, and mild oxidative conditions suggest that the present strategy might be useful for the assembly of bromochloromethyl functional groups in drug discovery.
