Palladium-catalyzed cycloaromatization of N-acyl-2-aminobiaryls, through a sequence of ortho CÀH bond activation/alkyne insertion/meta CÀH bond activation/alkyne insertion, was developed. An efficient synthesis of multiaryl-substituted naphthalenes, N-[2-(5,6,7,8-tetraarylnaphthalen-1yl)aryl]acetamides, was demonstrated using molecular oxygen as the sole oxidant. Furthermore, through Buchwald's synthetic protocol, two compounds were converted into corresponding fluorescent carbazoles in 30-40% yield by intramolecular CÀN bond formation.
Multicomponentr eactions of phosphines, enynedioates andc innamaldiminesg enerated 3phosphorus ylide g-lactamsh aving a1 ,3,5-hexatriene moiety with low activation energy barrier for 6p electrocyclization, through initial formation of 1,3-dipoles from the a(d')-Michael addition of phosphines to enynedioates.T he reactive 1,3-dipoles underwent addition to cinnamaldimines, lactamization, 6p electrocyclization ando xidation to give3 -phosphorus ylide oxindoles as platform molecules toward isatins and isoxazolinones.T he keys tep,6 pelectrocyclization, wasfurther examined by akinetic and acomputational study.Scheme 1. Tr aditional and our proposed synthetic strategy toward oxindoles 5.
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