Abstract
<jats:p>Converting simple acyclic compounds into N-heterocycles is a fascinating approach for the synthesis of functionalized heteroarenes. We achieved this transformation by using visible-light-induced carbyne capture with 2-amino benzoyl compounds under mild conditions. We have shown the synthesis of acyclic compounds to N-heterocyclic compounds, such as indoles, indolinones, and quinolines, by capturing carbyne via an in situ-generated α-aminocarbene from the chlorodiazirine reaction with 2-amino benzoyl compounds. The efficiency of this methodology demonstrates significant advances in carbene chemistry, generating a novel class of ⍺-aminocarbene intermediate, notably without the need for any catalysts. The reactivity was systematically investigated with electronically diverse substituted 2-amino benzoyl compounds and diazirines, leading to impressively efficient syntheses of highly functionalized N-heteroarenes. The synthetic utility of this method is also demonstrated by the synthesis of bioactive molecules, such as COX-2 inhibitors. Moreover, we have also shown the structural diversification of indoles into other heterocyclic compounds, accessing structurally relevant intermediates and incorporating various bioactive compounds onto the indole moiety. Mechanistic studies confirmed that this transformation proceeds via an ⍺-aminocarbene intermediate.</jats:p>