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Simple Halide-mediated Construction Of ?-peroxy Ketones And Amides

Posted on:2021-03-13Degree:MasterType:Thesis
Country:ChinaCandidate:Y YaoFull Text:PDF
GTID:2404330611494928Subject:Medicinal chemistry
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China's economic and social development has entered a new historical stage,and the Central Committee of the Communist Party of China has clearly proposed to build a resource-saving society.In the field of organic synthesis,the concept of green chemistry is more and more valued,and the development of higher atomic economy,milder conditions,and more environmentally friendly synthesis strategies is an important task and future development trend of organic chemistry.This paper mainly reports on two types of reactions developed based on the concept of green chemistry.1.The reactions involved in olefin compounds play a very important role in the development of organic synthesis.Difunctionalization of olefins can obtain multi-site reaction products in one step,and has obvious efficiency in the synthesis of various organic compounds.Therefore,this field is a research direction favored by chemists in recent years.Existing reports of difunctionalization of olefins mainly focus on reactions catalyzed by transition metals and some oxidants such as peroxides.We have developed a green synthesis strategy for ?-peroxone generation in one step using various aldehydes,olefins,and hydroperoxides as substrates under metal-free conditions.This strategy uses a simple and inexpensive halogenated tetrabutyl bromide.Ammonium was used as a catalyst to simultaneously construct new carbon-carbon bonds and carbon-oxygen bonds under mild conditions to obtain the target product ?-peroxone,and to directly obtain ?,?-epoxy ketone through a one-pot method.2.Amide units are important components in many important molecules such as drugs,proteins,natural products and functional materials.In the synthesis of all reported drug compounds,the structure of amide bonds accounts for 16%,so the construction of amide bonds is one of the hottest areas in the field of organic and medicinal chemistry.One-pot aldehyde oxidative amidation is a very good strategy for constructing amides,which has the advantages of high atomic economy,easy availability of raw materials,and high safety.However,most of the existing reports have some limitations,mainly including the use of transition metals and excess alkali.We have developed a green synthesis strategy for the amide compounds in one step using various aldehydes and amine hydrochloride as substrates under the conditions of metal-free and alkali-free participation.The strategy uses the simple halide tetrabutylammonium iodide as a catalyst.The conditions are mild and the adaptability to a large number of functional groups is good.
Keywords/Search Tags:olefin, difunctionalization, amide, oxidative amidation, simple halide
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