An FeCl-catalyzed [4 + 2] cycloaddition of vinyldiazo compounds with -acyliminium cations generated from 3-hydroxyisoindolinones is described. A series of diazo-containing isoindolo[2,1-]quinolinones were constructed in good yields with excellent diastereoselectivities, including those with three contiguous stereogenic centers. The resultant products were readily converted into various isoindolo[2,1-]quinolinone derivatives based on the rich chemistry of the remaining diazo functionality.
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Blue light-induced diazo cross-coupling: synthesis of allyldiazo compounds through reshuffling of functionalities.
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