A novel and highly practical reaction for the copper-catalyzed intermolecular cyanotrifluoromethylation of alkenes is presented here. This methodology provides a general and straightforward way to synthesize a variety of useful CF3-containing nitriles, which can be used for further preparation of pharmaceutically and agrochemically important compounds in synthetic organic chemistry.

A novel three-component strategy for the cyanotrifluoromethylation/azidotrifluoromethylation and carbocyclization of 1,6-enynes is developed. The reaction proceeds smoothly under a moderate temperature by using a copper catalyst, which provides a rapid and concise access to addition-carbocyclization products. Furthermore, the products obtained can be useful building blocks in discoveries of lead compounds and other biologically active CF3-containing heterocycles.

An iodine-promoted one-pot radical cyclization reaction of 1,6-enynes with sulfonyl hydrazides to provide five-membered and hexatomic ring sulfonylated products under the same conditions is established. This reaction proceeded smoothly in water and gave the corresponding products by using I2/TBHP instead of expensive and toxic catalysts with C-S and C-I bond formed in one step. This method also allowed easy access to significant functional sulfones for potential applications in medicinal and organic chemistry.

Two different cyclic amino esters are synthesized by palladium-catalyzed cross-coupling reaction of diazoesters with N-substituted-2-iodoanilines. Aryldiazoacetates lead to cyclic α-amino esters with an α-quaternary carbon centre in the presence of CO. Additionally, arylvinyldiazoacetates afford cyclic α,β-unsaturated γ-amino esters.

Photo-induced radical reductive dehalogenation of inactivated aryl/alkyl bromides and chlorides with a palladium complex is described. Reductive cyclization, dehalogenative deuteration, and radical addition process can be achieved smoothly.