Wang Chuan, Professor, University of science and technology of China research team: asymmetric alkylation of non activated olefins with nickel catalyst

Starting from simple olefins, organic chemists have great value in the synthesis of asymmetric bifunctional reactions In recent years, transition metals such as PD, Ni, Cu have been used to realize the bifunctional reaction of olefins However, the realization of asymmetric bifunctionalization, especially the unactivated alkenes, has always been a challenging topic, and there are only a few reported examples In 2014, Professor Gregory C Fu and his team first reported the asymmetric alkylation of nonactivated olefins with nickel homogeneous catalyst However, the redox neutral strategy is adopted, and the reaction requires equivalent organometallic reagents, which makes the synthesis of substrates difficult and the tolerance of functional groups low This problem can be effectively avoided by using the restore strategy However, there are few reports on the asymmetric effect of this strategy on the unactivated olefins Professor Wang Chuan's research team at the University of science and technology of China has been working on the methodology of bifunctional reduction of non activated olefins under the catalysis of nickel In 2018-2019, Professor Wang Chuan's team produced low-cost nickel complexes through the synergistic action of nickel salts, ligands and zinc powder, avoided the use of pre prepared organometallic reagents, and realized the aromatization of non activated olefins (chem SCI., 2019, 10, 1780) Recently, the group has realized the asymmetric alkylation of nonactivated olefins with the participation of nickel metal Relevant research results were published in angelw Chem Int ed (DOI: 10.1002 / anie 201901067) Prof Wang Chuan: Prof Wang Chuan, special professor and doctoral advisor From 2002 to 2007, he studied at the University of Gottingen in Germany; from 2007 to 2010, he studied at the Aachen University of technology in Germany; from 2011 to 2012, he worked at the Lich research center in Germany; from 2012 to 2015, he worked at the University of Chicago in the United States; from 2015 to 2016, he worked at the Purdue University in the United States; from 2016 So far, he has served as a special professor and doctoral advisor in China University of science and technology Main research fields: organic synthesis methodology, transition metal and organic small molecule catalysis, asymmetric synthesis and synthesis of bioactive molecules and natural products Research results: firstly, the brominated benzene 1a and 4-butyl acetate 2A containing terminal olefins were used as model substrates to optimize the reaction conditions After obtaining the best reaction conditions, the author further expanded the substrate (Fig 1) The functional groups such as hydroxyl, carbonyl, ester, cyano and halogen in the reaction substrate do not affect the reaction, and the derivatives of benzodihydroindene with quaternary carbon center can be synthesized with high corresponding selectivity They have the basic skeleton of a large number of drug molecules and bioactive molecules and have potential application value Fig 1 Substrate development (source: angelw Chem Int ed.) in order to further demonstrate the practicability of the method, the author carried out subsequent transformation of the generated products (Fig 2), and obtained ketones, lactones, hydrazone and olefins with complex structure and high corresponding selectivity Figure 2 Product transformation (source: angelw Chem Int ed.) Summary: Professor Wang Chuan's research team developed a nickel catalyzed asymmetric aryl alkylation of non activated olefins The reaction not only has a wide range of substrate applications and high corresponding selectivity, but also provides a new idea and method for the asymmetric bifunctional reaction of olefins catalyzed by nickel under reduction strategy This article was recently published on angelw Chem Int ed., the first author of which is Jin Youxiang, a doctoral student at the University of science and technology of China, and the corresponding author is Professor Wang Chuan 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.