Medium-sized rings (8~11 membered ring) and macrocycles (12-membered rings and above) are extremely important parts of drug and natural products.Meanwhile, they are widely used in the field of medicinal chemistry, organic chemistry and other fields.Developing simple, green and efficient protocol to synthesize medium-sized rings and macrocycles has attracted great interests from chemists in the recent years.The latest ring expansion/cyclization reaction in the synthesis of medium-sized ring and macrocyclic compounds in the past five years is reviewed, and the prospect of their future and development is also outlined.