A set of aryne and isocyanide-based novel multi-component coupling reactions is described. Crucial to these reactions is the silver-catalyzed addition of isocyanide with aryne species to form ortho nitrilium organosilver arene intermediates. The nitrilium moiety then reacts with a nucleophile followed by cyclization with or protonation of the organosilver moiety generates structurally diverse end products. Interception of the nitrilium ion with another isonitrile molecule leads to the formation of benzocyclobutene-1,2-diimines. On the other hand, interception of the nitrilium intermediate with nucleophiles containing a proton such as sulfonamides, alcohols, water, carboxylic acid results in the efficient formation of imidates, amidine, amide, imide derivatives. However, sequential addition of nitrile and isonitrile with aryne nicely led to nitrile3H-indol-3-imine compound.

Aryne-based multi-component coupling reactions enabled by silver-catalyzed addition of isonitriles

2019 Spring National Meeting

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