Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions

The state-of-the-art development of C-S, C-Se, and C-Te bond-formation research involving cross-coupling and addition reactions, are discussed. In 1998, after screening the available ligands, Zheng and coworkers found that Pd(OAc)2-BINAP-LiCl and in particular the Pd(OAc)2-Tol- BINAP system can catalyze cross-coupling reactions of various triflates. Krief and coworkers showed that NaH or CsOH can be a more convenient choice, although the reaction may require higher temperatures. Venkataraman and co-workers suggested using neocuproin as a ligand significantly extending the scope of the reaction to include aryl(hetaryl) iodides with both electron-donating and electron-accepting substituents as well as various alkyl and aryl thiols. Wang, Wu, and co-workers reported an excellent mechanistic study of a methylacetylene bisselenation on a Pd catalyst using theoretical calculations at the B3LYP level.