Silver-Catalyzed Coupling of Two C sp(3)-H Groups and One-Pot Synthesis of Tetrasubstituted Furans, Thiophenes, and Pyrroles.

Silver-catalyzed coupling of two C sp(3)-H groups to form 1,4-diketones have been developed for the first time. The resultant ketones then undergo cyclization to synthesize tetrasubstituted furans, thiophenes, and pyrroles from benzyl ketone derivatives in a one-pot reaction process. This highly-efficient synthetic method, which utilizes air as the terminal oxidant and readily accessible starting materials, displays a wide substrate scope and broad functional-group tolerance.