An efficient and convenient copper-catalyzed chalcogenation of imidazoheterocycles with sulfur/selenium powder and coumarinyl triflates has been described. This procedure provides a wide range of structurally diverse coumarinylthio-/coumarinylseleno-substituted imidazoheterocycles in good yields and with good functional group tolerance. Biological evaluation showed that the newly synthesized compound 6d possesses significant in vitro antiproliferative activities against human-derived esophageal, breast, stomach, and prostate cancer cell lines compared with the positive control, 5-fluorouracil.

•Pd/Cu-catalyzed reaction of 4-quinolinonyl triflates with benzothiazoles.•A range of 4-heteroaryl quinolinones are provided.•Some of the derivatives exhibit antiproliferative activity.A convenient and efficient approach for the synthesis of 4-heteroaryl quinolinones was developed via palladium/copper-catalyzed coupling reactions between 4-quinolinonyl triflates with benzothiazole/benzoxazole/thiazole/oxazole/benzimidazole. Biological evaluation revealed that some of the obtained products exhibited in vitro antiproliferative activities on human-derived live cancer cell lines.

A convenient and efficient approach for the synthesis of 2,3-dihydro-2,3′-bisindoles has been developed in good yields via dimerization of N-H indole derivatives. The synthetic utility of this approach was demonstrated by the rapid construction of bisindoles in gram-scale. Biological evaluation revealed that some of the obtained 2,3-dihydro-2,3′-bisindoles exhibited significant in vitro antiproliferative activities on human-derived lung, liver, stomach, and breast cancer cell lines.

•Palladium-catalyzed reaction of 4-coumarinyl triflates with indoles is described.•A range of 4-indolyl coumarins and 4-indolyl quinolinones are provided.•Some of the derivatives exhibit good antiproliferative activity.A convenient and efficient approach for the synthesis of 4-indolyl coumarins and 4-indolyl quinolinones was developed via palladium-catalyzed coupling reactions between 4-coumarinyl triflates/4-trifluoromethanesulfonyloxyquinolinones and indoles. Biological evaluation revealed that some of the obtained products exhibited in vitro antiproliferative activities on human-derived prostate, stomach, lung, breast cancer cell lines.

A convenient and efficient approach for the synthesis of α,α-(bisallyl and bispropargyl)-substituted amines has been developed in good yields via Zn-promoted aza-Barbier-type reactions of N-sulfonyl imidates with various allyl and propargyl reagents. The synthetic utility of this approach was demonstrated by the rapid construction of pyrrolidine derivatives.