Development of atom-economical multicomponent coupling reactions via hypervalent ate complexes

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We have developed multicomponent coupling reactions, where zwitterions derived from arynes and neutral nucleophiles are trapped by alkynyl or perfluoroaryl bromides. These reactions proceed through formation of hypervalent ate complexes generated from aryl anion moieties of the zwitterions and bromine moieties of the organic bromides. Isocyanides and cyclic ethers (THF, oxetane) can serve as neutral nucleophiles in the reaction. Furthermore, total synthesis of a biologically active molecule has been achieved by using the oxetane-derived product.