Zhang Ao group and Lu Xiaojie group of Shanghai Institute of medicine have made new progress in the construction and application of diverse carbon heterobond reactions

Recently, iscience, a subsidiary of cell publishing house, published the latest scientific research results of constructing diverse carbon heterobonds based on C-N bond cutting, which was jointly completed by Zhang Ao group and Lu Xiaojie group of Shanghai Institute of medicine, Chinese Academy of Sciences Carbon heterobonds (such as C-O, C-N, C-S, C-Se, c-Si, c-ge, c-sn, etc.) are the most common chemical bonds in organic molecules Their construction and cleavage are important steps in the synthesis of natural products, drug molecules, functional materials, etc., and also the key to further functional group transformation Up to now, the method of constructing various carbon heterobonds is usually based on the cross coupling reaction of aryl halides and heteroatom nucleophiles under the catalysis of transition metals However, there are many problems in this method, such as the harsh conditions, the substrate needs to be functionalized in advance, transition metal residues and so on Zhang Ao research group of Shanghai Institute of medicine has carried out many years of research on the new method of efficient construction of carbon heterobonds, and successively realized the construction of aromatic inter ring carbon nitrogen bonds based on the activation of inert C-H bonds (j.am.chem.soc 2016, 138, 8470; ACS catalysis, 2016, 6, 769; org Lett., 2017, 19, 3199) and efficient construction of carbon oxygen bond (angel W chem Int ed., 2018, 57, 3641) based on aromatic amine substrate On this basis, the group further expanded the new chemical reaction space with aryl quaternary ammonium salt as the substrate, and realized the rapid and efficient construction of various carbon heterobonds (C-S, C-Se, c-Si, c-ge, c-sn, C-N) without transition metal catalysis under extremely mild conditions This method is not only suitable for the later structural modification of active natural products and drug molecules, but also for the construction of fluorescent probe molecules through drug click reaction, which can be used for the detection of specific biological processes in vivo Finally, the method was successfully applied to DNA compatible functional group reaction by combining with Lu Xiaojie, and the establishment of DNA coding compound library was realized At present, the compounds with antitumor activity have been screened from del library, and the follow-up work is in progress The research work was completed with the joint efforts of Wang Dongyu, postdoctoral of Zhang Ao research group, and Lu Xiaojie, postgraduate of research group Wang Dongyu is the first author of the paper (iscience, 2019, 15, 307-315) The research work was supported by researcher Zhou Hu and his research group Meng Qian from the Analytical Chemistry Research Office of the Institute of medicine The project was supported by NSFC, Ministry of science and technology, Chinese Academy of Sciences, Shanghai Municipal Science and Technology Commission, etc.