Research group of Professor Song Qiuling of Huaqiao University: new progress in visible light induced functional group reaction of alkenes

Introduction: olefins are easy to obtain and have various reaction modes A series of complex organic compounds can be synthesized through their functional group reaction Therefore, their research has been paid more attention by chemists In recent years, visible light induced organic chemical reactions have developed rapidly, which are characterized by mild conditions, various reaction modes and strong tolerance of functional groups This type of reaction can be used to synthesize a series of compounds which can not be prepared by conventional reaction, so it can be said that it is a very promising synthesis strategy Recently, song Qiuling group of the new generation material transformation Research Institute of Huaqiao University has made some new achievements in this field Song Qiuling research group profile song Qiuling research group was founded in May 2013 and was established as a new generation of material transformation Institute at the end of the year At present, there are one professor, one distinguished professor (foreign), three lecturers, one postdoctoral, six doctors and 15 masters The team leader, Professor Song Qiuling, was selected into the National Youth Millennium Program in 2012 At present, the research group is mainly engaged in free radical chemistry, organoboron chemistry, organometallic chemistry and functional organic molecule synthesis Since its establishment, the research group has published more than 60 papers in the international journals such as angelw Chem Int ed., org Lett., green chem., chem Comm., chem - EUR J., adv synth Catalyst., among which 20 articles have been selected as the front cover or back cover by green chem., chem Commun., adv.synth Catalyst., org Chem Front., etc Introduction to Professor Song Qiuling, Professor, doctoral supervisor In 1998, he graduated from the Department of chemistry of Zhengzhou University with a bachelor's degree and studied under Professor Wu Yangjie; after graduation, he was sent to the school of chemistry and molecular engineering of Peking University for a master's degree and studied under Professor Xi Zhenfeng; in August 2002, he went to Princeton University for a doctor's degree and graduated in December 2006 with Professor Robert Pascal After graduation, he directly entered the industry and worked in the pharmaceutical industry for nearly five years; in 2012, he was introduced by overseas Chinese University and was selected into the National Youth thousand talents program in August of the same year, and was employed as a professor and doctoral supervisor Leading scientific research achievements: visible light induced functionalization of olefins; oxidative quenching is the mechanism experienced by most visible light induced trifluoromethylation of olefins These reactions generally require the use of CF 3I, CF 3so2cl, The further application of this kind of reaction is limited by the inconvenience of operation of umemoto reagent and togni reagent or the difficulty of obtaining trifluoromethylation reagent Recently, song Qiuling group used CF 3so2na as the trifluoromethylation reagent and phso2sr as the sulfurization reagent to successfully realize the visible light induced sulfotrifluoromethylation reaction (chem Commun., 2017, 53, 8968-8971) The mechanism study shows that the reaction undergoes the reduction quenching process, and the reaction is characterized by simple operation, mild reaction conditions and wide range of substrates (Fig 1) Figure 1: light induced trifluoromethylation of olefins (source: chem Commun., 2017, 53, 8968-8971) was followed by a visible light catalyzed decarboxylation alkylation of enol silyl ethers to ketones (org Lett 2018, DOI: 10.1021 / ACS Orglett 7b03587) In this reaction, n-acyloxy-o-phenylsuccinimide derived from alkyl carboxylic acid was used as the source of alkyl radical, and a series of functionalized arylalkylketones were synthesized by the addition of enol silyl ethers in the redox neutral condition Figure 2: visible light catalyzed decarboxylation and alkylation of enols and silanes to ketones (source: org Lett, Doi: 10.1021/acs.orglett.7b03587) substrate adaptability study showed that n-acyloxyphthalimide derived from primary and secondary alkylcarboxylic acids showed better activity in this reaction, while n-acyloxyphthalimide derived from benzyl carboxylic acid and tertiary alkylcarboxylic acid showed lower activity This may be due to the strong stability and steric hindrance of benzyl radicals and tertiary alkyl radicals In addition, the reaction has good tolerance to halogen, alkynyl, ester, carbonyl and other groups It is worth mentioning that Fenbufen, indomethacin and other drug molecules, stearic acid, dehydrocholic acid and other naturally occurring carboxylic acid compounds also show excellent reactivity in the reaction, further proving the practicability of the reaction (Fig 3) When n-acyloxyphthalimide derived from γ - carboxylic acid is used as the source of free radicals, the reaction products are 1,5-dicarbonyl compounds with important synthesis applications (Fig 4) Figure 3: substrate development of carboxylic acid derivatives (source: org Lett., DOI: 10.1021 / ACS Orglett 7b03587) Figure 4: substrate development of enol silicone ether compounds (source: org Lett, Doi: 10.1021/acs.orglett.7b03587) the above research work has been strongly supported by the "youth thousand talents" program of the Central Organization Department, the natural science foundation of Fujian Province, the science and technology innovation and Leading Talents Program of Huaqiao University, and the graduate innovation fund of Huaqiao University The above work is mainly completed by Dr Kong Weiguang of the new generation material transformation Institute Editor's note: with the increasing attention paid to the elements of science and technology in economic life, China has ushered in the "node of the outbreak of science and technology" Behind the progress of science and technology is the cultivation 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 They abandon impetuosity and concentrate on research The data shows that the number of patent applications and papers in China's chemical field has ranked the top in the world, especially in the field of chemical drugs During the 12th Five Year Plan period, international patents have ranked the third in the world, and the total number of papers has ranked the second in the world To this end, CBG information adopts the 1 + X reporting mechanism CBG information, chembeango app, chembeango official microblog, CBG wechat subscription number and other platforms jointly launch the "CBG characters" column We will approach the representative research groups in China, pay attention to their research, listen to their stories, record their demeanor, and explore their research spirit Related papers: http://pubs.rsc.org/en/content/article landing/2017/cc/c7cc03520a ා! Divabstract http://pubs.acs.org/doi/10.1021/acs.orglett.7b03587 song Qiuling research group homepage: http://sqlktz.ceomoo.cn/index.php "CBG people" column: Today, science and technology elements are increasingly valued in 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, chembeango app, chembeango official microblog, CBG wechat subscription number and other platforms jointly launch the "CBG characters" column, approach the domestic representative research group, pay attention to their research, listen to their stories, record their demeanor, and explore their research spirit.