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    Home > Professor Guo Chang, University of science and technology of China research team: Lewis acid catalyzed asymmetric electrochemical alkylation

    Professor Guo Chang, University of science and technology of China research team: Lewis acid catalyzed asymmetric electrochemical alkylation

    • Last Update: 2019-04-16
    • Source: Internet
    • Author: User
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    Lead electrochemistry and asymmetric catalysis are the frontier and research hotspot of organic chemistry, and they are paid more attention in the field of organic synthesis In recent years, electrochemistry, as a new platform for organic synthesis, has made remarkable progress With the advantages of mechanochemistry, it can further expand the activation model, reaction type and substrate adaptability of asymmetric catalysis, solve the difficult problems in traditional asymmetric catalysis, and further expand the application scope of asymmetric catalysis; at the same time, it can also be used as a platform for mechanochemistry The synthesis of chemistry provides new ideas and new ideas Therefore, it is a highly efficient and green synthesis strategy to combine asymmetric catalytic synthesis with organic synthesis and develop asymmetric electrocatalytic reaction However, it is still a challenge to achieve efficient and highly selective synthesis by asymmetric electrochemical reaction Recently, Guo Chang, Professor of University of science and technology of China, has realized the asymmetric electrochemical alkylation of Lewis acid by combining electrochemistry with chiral Lewis acid catalytic system and using asymmetric C-H activation / free radical cross coupling reaction Relevant research results were published in angelw Chem Int ed (DOI: 10.1002 / anie 201901801) Prof Guo Chang is a special professor and doctoral supervisor of China University of science and technology From 2003 to 2007, he studied at the University of science and technology of China, from 2007 to 2013, he studied at the University of science and technology of China, from 2013 to 2017, he engaged in postdoctoral research at the University of Minster, Germany, from 2017 to 2018, he served as the special researcher and doctoral supervisor of Hefei National Research Center for micro scale material science, University of science and technology of China, 2018 He has been a special professor and doctoral supervisor of Hefei National Research Center of micro scale material science, University of science and technology of China since Main research directions: Based on the research of new asymmetric catalysis, the direct chiral functionalization of inert chemical bond is developed, the chiral catalysis model is established, the reaction activity and selectivity are improved, and these methodologies are applied to the synthesis of natural products, and the modern organic synthesis chemistry with high efficiency, atomic economy and environmental friendliness is developed Leading research results: firstly, 2-acylimidazole 1a and 2,4,6-trimethylphenol 2A were used as model substrates to optimize the reaction conditions After obtaining the best reaction conditions, the author further expanded the substrate (Fig 1) A series of alkylation products with excellent enantioselectivity can be obtained by the conversion of 2-acylimidazolyl phenyl with different electron absorption or electron substitution groups In addition, naphthyl or thiophenyl imidazole can also react well, which proves the diversity of substituents The reaction of 2 - (phenylthio) acylimidazole can also be carried out, with medium yield and enantioselectivity It is worth noting that when imidazole has different kinds of N-substituents, the product can also be obtained with good yield and excellent enantioselectivity Fig 1 Substrate development (source: angelw Chem Int ed.) later, the author studied a series of asymmetric electrochemical reactions of p-methylphenol derivative 2 (Fig 2) A variety of p-methylphenol derivatives 2 can obtain the alkylation adducts with high yield and excellent enantioselectivity Figure 2 Substrate development (source: angelw Chem Int ed.) in order to further demonstrate the practicability of the method, the author conducted a subsequent transformation of the generated product (Figure 3), and compound 41 can be converted into a target compound with antibacterial activity Figure 3 Product transformation (source: angelw Chem Int ed.) Summary: Professor Guo Chang's research team reported an asymmetric electrochemical alkylation reaction catalyzed by Lewis acid Asymmetric electrosynthesis can be realized by coupling the free radicals of Lewis acid and the free radicals of benzyl radical driven by electrochemical oxidation, which can be used to synthesize the target chiral compounds with antibacterial activity It is proved that this kind of reaction has a wide range of substrate application and high enantioselectivity This article was recently published on angelw Chem Int ed., the first author of which is Zhang Qinglin, a graduate student of China University of science and technology, and the corresponding author is Professor Guo Chang Nowadays, people and scientific research have been paid more and more attention in the economic life China has ushered in the "node of science and technology explosion" Behind the progress of science and technology is the work of countless scientists In the field of chemistry, in the context of the pursuit of innovation driven, international cooperation has been strengthened, the influence of Returned Scholars in the field of R & D has become increasingly prominent, and many excellent research groups have emerged in China For this reason, CBG information adopts the 1 + X reporting mechanism CBG information, chembeangoapp, chembeango official microblog, CBG wechat subscription number and other platforms jointly launch the column of "people and scientific research", approach the domestic representative research group, pay attention to their research, listen to their stories, record their demeanor, and explore their scientific research spirit.
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