Silver-Mediated [2 + 2 + 1] Cyclization Reaction of Diynes with Elemental Selenium/Sulfur to Synthesize 3,4-Substituted Cyclopenta[ c]selenophenes/Cyclopenta[ c]thiophenes

An efficient and atom-economical silver-mediated [2 + 2 + 1] cyclization protocol for the synthesis of 3,4-fused-ring-substituted and 2,5-unsubstituted selenophenes or thiophenes has been developed. Two C-Se/C-S bonds and one C-C bond were rapidly constructed in one step. Readily accessible substrates, commercially available elemental selenium/sulfur, and good functional group tolerance make this procedure attractive for the synthesis of π-conjugated material molecules.