17215-77-9Relevant academic research and scientific papers
A Simple and Efficient Method for the Preparation of α-Halogenated Ketones Using Iron(III) Chloride and Iron(III) Bromide as Halogen Sources with Phenyliodonium Diacetate as Oxidant
Tang, Shi-Zhong,Zhao, Wenshuang,Chen, Tao,Liu, Yang,Zhang, Xiao-Ming,Zhang, Fu-Min
supporting information, p. 4177 - 4183 (2017/12/18)
α-Halogenated ketones are both unique structure moieties existing in biologically natural products and valuable synthetic intermediates for the preparation of functional molecules. An efficient and scalable method for the preparation of α-halogenated ketone using iron (III) chloride and iron (III) bromide as halogen sources with phenyliodonium diacetate as oxidant has been developed, featuring mild reaction conditions, environmentally friendly reagents, and wide substrate scope. Notably, the three-step synthesis of drug prasugrel was achieved using this developed method as a key step with 30% yield on gram-scale. Additionally, the reaction mechanism involving chloride cation was proposed based on some preliminary control experiments. (Figure presented.).
Efficient Synthesis of α-Chloroketones Catalyzed by Fluorous Hydrazine-1,2-Bis(Carbothioate) Organocatalyst
Zhu, Yi-Wei,Shi, Yi-Xin
, p. 570 - 574 (2016/03/01)
A novel and recoverable fluorous hydrazine-carbothioate organocatalyst was prepared. It could catalyze α-chlorination of alkyl ketones with N-chlorosuccinimide as chlorine source under mild reaction conditions. The reaction afforded the corresponding α-ch
The use of sodium chlorate/hydrochloric acid mixtures as a novel and selective chlorination agent
Moon, Byung Seok,Choi, Han Young,Koh, Hun Yeong,Chi, Dae Yoon
experimental part, p. 472 - 476 (2011/12/04)
Sodium chlorate/hydrochloric acid mixtures were used to chlorinate activated arenes and the α-position of ketones. This chlorination method was used to produce selectively mono-, di-, and trichlorinated compounds by controlling the molarity of sodium chlorate. This reagent proved to be much more efficient and easier to handle than chlorine gas.
Thiourea catalysis of NCS in the synthesis of α-chloroketones
Mei, Yujiang,Bentley, Paul A.,Du, Juan
, p. 3802 - 3804 (2008/09/21)
Thiourea catalyzes NCS α-chlorination of alkyl ketones to provide α-chloroketones in very high yields at exceptionally rapid reaction speeds.
2-Chloropyridazin-3(2H)-ones as electrophilic chlorinating agents: Effective α-chlorination of active methylene/methine compounds
Park, Yong-Dae,Kim, Jeum-Jong,Cho, Su-Dong,Lee, Sang-Gyeong,Falck, J. Russell,Yoon, Yong-Jin
, p. 1136 - 1140 (2007/10/03)
2,4,5-Trichloro- (2a) and 2,4-dichloro-5-methoxypyridazin-3(2H)-one (2b) are novel electrophilic chlorinating agents. α-Chlorination of active methylene/methine compounds with 2 in the presence of either Lewis or protonic acids in dichloromethane (for Lewis acid) or water (for protonic acid or none) at room temperature gave also selectively α-monochlorides and/or α,α-dichlorides in good to excellent yields.
The oxidation of alcohols in N-oxyl-immobilized silica gel/aqueous NaOCl disperse systems. A prominent access to a column-flow system
Tanaka, Hideo,Chou, Jingyu,Mine, Machiko,Kuroboshi, Manabu
, p. 1745 - 1755 (2007/10/03)
The oxidation of alcohols was performed successfully in a disperse system with N-oxyl-adsorbed or immobilized silica gel as a disperse phase and aqueous NaOCl as a disperse medium. In the disperse system, the oxidation of sec-alcohols afforded the corresponding ketones, while prim-alcohols were oxidized to aldehydes and/or carboxylic acids depending on their structures and reaction conditions. The N-oxyl-immobilized silica gel was recovered and repeatedly used without a significant change in the product yields. A column-flow system was also investigated for the oxidation of alcohols by use of a newly devised column packed with the N-oxyl-immobilized silica gel.
