Palladium-catalyzed cyclization of 1-alkynyl-8-iodonaphthalene and double isocyanides for the synthesis of acenaphtho[1,2-b]pyrroles

Catalytic metal-enabled story of isocyanides for use as “C1N1” synthons in cyclization: beyond radical chemistry

“…Reaction scope exploration showed that the reaction of 1-iodo-8-( p -tolylethynyl)naphthalene 64 with benzyl isocyanide 65 provided a by-product 66 in 31% yield (Scheme 19). 35 In this process, the formation of the imide group was ascribed to β-hydride elimination of intermediate 58-E′ , which could support the mechanism presented in Scheme 17.…”

Iron/photoredox dual catalysis for acyl nitrene-based C–O bond formation towards phthalides

“…As presented in Scheme 1, eqn (b), it is hypothesized that iron catalysis enabled the formation of iron acyl nitrene A from 2-alkylbenzamide 1 . 5 a , b ,10 The formation of ferric acyl nitrene species A initiated the HAA step. By HAA transformations, conversion of the intermediate A provided an intermediate C .…”

Palladium-Catalyzed Preparation of N-Substituted Benz[c,d]indol-2-imines and N-Substituted Amino-1-naphthylamides

“…As we all know, the rapid development of palladium catalysis has tremendously increased the versatility of isocyanides-based transformation . As part of our research interests in the controllable synthesis of naphthalene condensed heterocyclic compounds, we question whether a palladium-catalyzed reaction between 8-halo-1-naphthylamines and isocyanides could be achieved (Scheme d). Therefore, we would like to develop an intramolecular palladium-catalyzed controllable synthesis of benz­[ c , d ]­indol-2-imines using isocyanides as the C1 synthons.…”