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High selectively oxidative bromination of toluene derivatives by the H_2O_2-HBr system

Chinese Chemical Letters 2011年第4期22卷 382-384页

作者： Jie Ju Yu Jin Li Jian Rong Gao Jian Hong Jia Liang Han Wei Jian Sheng Yi Xia Jia The State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology Zhejiang University of TechnologyHangzhou 310032China

An aqueous solution of hydrogen peroxide and hydrogen bromide illuminated by a 60 W incandescent light bulb serves as a source of bromine *** substituted toluenes（NO2,Cl,Br,H,CH3） were high selectively brominated at the benzyl position for monobromination in CH2C12 at ice water with catalyst *** simple but effective bromination of toluene derivatives with an aqueous H2O2-HBr system is characterized with the use of inexpensive reagents and a lower impact on the environment, which make it a good alternative to the existing bromination methods.

关键词： Oxidative bromination toluene derivatives H2O2-HBr

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Oxyacylation of Carbonyl Compounds with toluene derivatives

Oxyacylation of Carbonyl Compounds with Toluene Derivatives

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中国化学会第十三届全国有机合成化学学术研讨会

作者： Li Cheng-Liang Jia Xue-Shun Department of Chemistry Shanghai University

The selective α-oxygenation of carbonyl compounds constitutes an important reactivity mode in organic synthesis,as the resultant α-oxygenated carbonyl moieties are common structural motifs in many natural products and biologically active molecules.1 As such,transformations toward the preparation of such skeletons have been extensively investigated in the past decades.2 Among them,the selectiveα-hydroxylation of Csp 3-H of ketones seems to provide a direct and efficient *** the other hand,α-oxyacylation of carbonyl compounds has also received considerable attention from the synthetic ***,these compounds could be prepared from α-halocarbonyl compounds 4 and the oxidative coupling of carbonyl compounds with highly toxic heavy-metal oxidants.5 To overcome the drawbacks of traditional methods,hypervalent iodines and other oxidants were widely investigated to promote the α-oxyacylation of *** recently,reactions using other oxyacylative reagents other than carboxylic acids have also been *** with the popularity of ketone α-oxyacylation,successful examples with other carbonyl compounds are still *** impressive achievements have been made to date,most of the reported examples suffered from harsh conditions,a limited substrate scope,or highly toxic *** a result,there is still a continuing demand to develop novel and environmentally benign methods with a broad scope as well as simple and readily available starting *** a continuation of our previous research,6 herein we report that,in the presence of TBAI the reactions between carbonyl compounds and simple arylmethanes could furnish the C-O bond formation using toluene derivatives as an oxyacylative precursor.

关键词： oxyacylation carbonyl compounds toluene derivatives

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Construction of Some Chemical Bonds via Methylarenes sp3 C-H Reaction

Construction of Some Chemical Bonds via Methylarenes sp3 C-H...

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中国化学会第十四届全国有机合成化学学术研讨会

作者： Chengliang Li Jian Li Xueshun Jia Department of Chemistry Shanghai University

toluene and its derivatives are considered to be the simplest and readily available starting materials in nature,which has made them highly valuable building blocks in organic synthesis. A careful literature survey revealed that reactions using toluene derivatives as a benzyl precursor were very popular,thus offering a new opportunity for the formation of carbon–carbon and carbon–heteroatom bonds. Additionally,using arylmethanes as an acyl source was another research focus and much progress has been achieved. In this regard,we became interested in exploring novel reactions using toluene derivatives as versatile building ***,we reported the coupling reaction of toluene derivatives with isocyanides and carbonyl compounds,*** a continuation of our previous research, herein we wish to disclose our work on methylarenes spC-H reaction to construct the carbon–carbon and carbon–heteroatom bonds.

关键词： toluene derivatives methyl sp~3 C-H reaction

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