This project belongs to the field of ldquo; Organic Synthetic Chemistry rdquo; in the discipline of ldquo; Organic Chemistry rdquo;. The oxidation of hydrocarbons is one of the most important and basic reactions in organic synthetic chemistry. It is of great significance to develop new reactions for oxidative functionalization of hydrocarbons with high efficiency, high stereoselectivity and selectivity by proposing new concepts and new strategies. Supported by the Ministry of Science and Technology, the Natural Science Foundation of China and the Shanghai City Science and Technology Commission, this project focuses on metal-catalyzed selective functionalization of olefins and alkyl aromatic hydrocarbons, focusing on exploring ldquo; asymmetric control of active free radicals in free radical chemistry and ldquo; Catalytic fluorination is two extremely challenging scientific problems; Through interdisciplinary research, ldquo; transition metal catalysis is combined with ldquo; free radical chemistryrdquo; and ldquo; fluorine chemistryrdquo; Combined with this, a series of new reactions of transition metal-catalyzed asymmetric conversion and oxidative fluorination of free radicals have been developed using the high activity of high-valence metal-organic intermediates; ldquo; metal-catalyzed free radical relay rdquo; The new concept has developed the asymmetric cyanation reaction of the sp3 carbon-hydrogen bond, achieving a major breakthrough in this field, and providing new ideas and ways for the later modification of drug molecules. (1) Based on the reaction characteristics of high-valent copper species, the concept of ldquo; metallic copper catalyzed free radical relay rdquo; was proposed for the first time. By converting uncontrollable free radicals into selectively controllable high-valent organic copper intermediates, copper-catalyzed asymmetric free radical reactions have been developed, realizing the asymmetric cyanation of the benzyl carbon-hydrogen bond of alkyl aromatic hydrocarbons, directly converting simple petroleum products into chiral drug precursors, and achieving a major breakthrough in this field. (2) Based on the high activity of high-valent palladium intermediates, the selective fluorination of olefins and related reactions were achieved through the ldquo; metal palladium-catalyzed oxidative fluorination rdquo; strategy for the first time using readily available nucleophilic fluorination (fluorine-containing) reagents; a new concept of ldquo; fluoropaladylation of olefins/alkynes rdquo; was proposed, the selective fluorination of olefins was developed, and a new mechanism for the selective formation of carbon-fluorine bonds was clarified; new ideas and methods were provided for the efficient synthesis of fluorine-containing heterocyclic compounds. (3) Based on the characteristics of high-valent palladium intermediates that are easy to reduce and eliminate, an efficient catalytic system has been developed to realize the selective amination of allylic carbon-hydrogen bonds of terminal olefins, which solves the problems of low catalytic efficiency and substrate isomerization in previous reactions; and a new model of activation of the sp3C-H bond of nitrile compounds has been developed to realize the bi-hydrocarbon activated olefin bifunctionalization reaction. So far, as corresponding author, he has published 87 SCI papers, including Science(1), Acc. Chem. Res. (2 articles), J. Am. Chem. Soc. (18 Articles), Angew. Chem. Int. Ed. (17 articles), etc. In total, he cited 4167 times, with a maximum of 327 times for a single article; he cited 1367 times for 8 representative papers, with an average of 171 times. Obtained 5 invention patent authorizations from China. Eighteen doctoral students were trained, of whom 3 received Outstanding Doctoral Dissertations from the Chinese Academy of Sciences, 1 received the Special Award of the President of the Chinese Academy of Sciences, 2 received the President's Award of the Chinese Academy of Sciences, 1 was selected into the Thousand Young Talents Program, and 2 were selected into the Shanghai City ldquo; Pujiang Talents Program., 4 are professors/associate professors in universities. The first person to complete the project gave conferences or invited reports 64 times at domestic and foreign academic conferences such as Gordon Research Conferences; he was funded by the 2012 National Natural Science Foundation of China, was awarded as the Leading Talent of Shanghai City in 2017, the China Chemical Society-BASF Youth Knowledge Innovation Award, the National Ten Thousand Talents Program, and the 2019 Humboldt Bessel Research Award in Germany. The research results of the project are of great significance to the fields of metal organic chemistry/fluorine chemistry/asymmetric free radical chemistry, etc., and promote the research and development of organic chemistry.