Gold- and silver-catalyzed intramolecular annulation and rearrangement of aniline-linked 1,6-enynes containing methylenecyclopropanes

Abstract

Gold- and silver-catalyzed intramolecular annulation and rearrangement of aniline-linked 1,6-enynes containing methylenecyclopropanes have been reported in this paper, affording the corresponding 1,2-dihydroquinolines containing a cyclobutene moiety as the major products upon gold catalysis and the corresponding 1,2-dihydroquinolines containing a methylenecyclopropane moiety as a single product upon silver catalysis in moderate to good yields under mild conditions. In the gold-catalyzed cycle, the formation of 1,2-dihydroquinolines containing a cyclobutene moiety may proceed through cyclopropyl gold-carbene intermediate twice.