Project team of Professor Zhou qianghui of Wuhan University: a dual task methylation strategy with palladium and norbornene

Introduction catelani reaction is a kind of domino reaction that directly functionalizes the inactive long-range hydrocarbon bond on the aromatic ring under the joint action of palladium and norbornene Based on this strategy, Professor Zhou qianghui's research group has developed a new catelani reaction with epoxy compounds as alkylating agents, which is used to construct heterocyclic framework of heterochroman and benzodihydrofuran (angel Chem Int ed 2018, 57, 3444 – 3448, org Chem Front., 2018, 5, 2533 – 2536) Using this strategy, they have also completed the efficient construction of benzo ring molecular skeleton, such as tetrahydronaphthalene, dihydroindene compounds (ACS catalyst, 2018, 8, 4783 – 4788) and tetrahydroisoquinoline (angel Chem Int ed 2018, 57, 10980 – 10984) with benzyl quaternary carbon center In addition, they have developed a series of new palladium initiated "borono catelani" reactions (angel Chem Int ed 2018, 57, 7161 – 7165, chem SCI., 2019, 10, 8384 – 8389, org Lett 2019, 21, 3323 – 3327) Recently, Professor Zhou qianghui's research group has made a new breakthrough in this field They have developed a new dual tasked C-H methylation strategy, and the related achievements have been published on J am Chem SOC (J am Chem SOC 2019, 141, 15986 − 15993) Figure 1 Front cover of the Journal (source: J am Chem SOC.) introduction to Professor Zhou qianghui's research group Professor Zhou qianghui's research group has been committed to efficient and practical synthesis methodology and total synthesis research Since its establishment, the research group has published 17 papers in internationally renowned academic journals, including NAT Commun., J am Chem SOC., angel Chem Int ed., chem SCI., ACS catalyst And other internationally renowned journals The research work has been widely concerned and recognized by peers at home and abroad, and has been highlighted by synfacts, organic chemistry and organic chemistry portal for many times Prof Zhou qianghui, Professor of School of chemistry and molecular science, Wuhan University, part-time researcher and doctoral supervisor of higher research institute From 2005 to 2010, he studied at Shanghai Institute of organic chemistry, Chinese Academy of Sciences, under the guidance of researcher Ma Dawei (one of the winners of material science award of "future science award" in 2018) He then went to Scripps Institute for postdoctoral research (co Tutor: Professor Phil Baran, MacArthur Genius Award winner, academician of the American Academy of Sciences) During his doctoral and postdoctoral work, he published 7 papers in science, J am Chem SOC., angelw Chem Int ed and other professional top journals In 2015, he joined the school of chemistry and molecular science of Wuhan University to carry out independent scientific research Homepage of the research group: http://qhzou.whu.edu.cn Leading scientific research achievements: palladium and norbornene double task methylation strategy A large number of studies have shown that the introduction of one or more methyl groups into candidate drugs can significantly regulate their physiological activities, improve their half-life, solubility and target selectivity, and sometimes even turn an agonist into an antagonist This effect is called "magic methyleffect" by the medical community Therefore, the methylation of bioactive molecules is one of the most commonly used strategies in the development of new drugs At present, the methylation strategies can only achieve a single methylation, and it is difficult to introduce isotope labeled methyl into the molecule, although it is also of great significance to introduce isotope labeling into candidate drugs through methylation Figure 2 The importance of methylation in Pharmaceutical Chemistry (source: J am Chem SOC.) in view of the shortcomings of existing methylation methods, Zhou qianghui group developed a new dual tasked C-H methylation strategy In this strategy, the cheap methyl p-toluenesulfonate or trimethyl phosphate is used as the methylation reagent Through the synergistic catalysis of palladium and norbornene, while the ortho-c-h bond methylation of aryliodide is realized, six different types of termination reactions can be carried out simultaneously in situ, thus a series of very useful methyl substituted aromatics are synthesized In addition, deuterium and carbon 13 isotope labeled methyl groups can be easily introduced by using methyl deuterium toluene sulfonate or methyl p-toluene sulfonate labeled with carbon 13 as reagents Figure 3 Dual task methylation strategy (source: J am Chem SOC.) the reaction has good applicability and functional compatibility It is very important for the future biological and medical research Therefore, this method is expected to be widely used in the research and development of new drugs At present, the research has applied for patent protection Figure 4 Late methylation of phenylglycine derivatives and aromatic drug molecules (source: J am Chem SOC.) was recently published on J am Chem SOC (J am Chem SOC 2019, 141, 15986 − 15993) Gao Qianwen, a 2019 doctoral student from the school of chemistry and molecular science of Wuhan University, is the first author of the paper, and Professor Zhou Qianhui is the corresponding author The above research work is supported by NSFC, Wuhan University startup fund and China Postdoctoral Science Fund 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 website, chembeangoapp, chembeango official micro blog, CBG information wechat subscription number and other platforms jointly launch the column of "people and scientific research", approach the representative research groups in China, pay attention to their research, listen to their stories, record their demeanor, and explore their scientific research spirit.