Air oxygen oxidation cross coupling is one of the most important and economical coupling reactions, using air as a oxidant replacing external oxidants can construct C—C and C—X (X=N, O, S or P) bonds through oxidative coupling of C−H bonds, which can effectively introduce new functional groups into heterocyclic compounds and have practical value for the development of drugs, agricultural chemicals, and functional materials. This paper reviews the research progress of air oxygen−mediated cross−oxidative coupling reactions of C—H bonds, with a particular focus on the synthetic systems of nitrogen−containing heterocyclic compounds. It elaborates novel strategies for the construction of C—C, C—N, and C—P bonds in heterocyclic compounds under transition−metal catalysis (e.g., nickel, palladium, copper, and iron), as well as metal−free and photocatalytic systems. The reaction characteristics, substrate applicability, and reaction mechanisms of various catalytic systems are summarized, and the research achievements including rare−earth−catalyzed coupling reactions between heterocycles and ethers as well as the novel amination reaction via aldehyde group exchange are also outlined. The environmentally friendly air oxidation reaction is expected to be further applied in industrial production.

air oxygen  /  oxidative cross coupling  /  heterocyclic compounds  /  functional groups  /  environmentally friendly