Indole ring expansion into quinolines with TMSCCl3/TMSCBr3

Reactivity adaptation speciation perceives reactants as a dynamic supply pool of shifting reactive units for opportunistic reactivity-matching diverse-manifold pathways to varied reactivity patterns, revealing the title C2C3–CCl/CBr insertion ring expansion of indole into quinoline, N1–H–TMS nucleophilic substitution, and N1–H–CCl₃ nucleophilic substitution for the indole–TMSCCl₃/TMSCBr₃ reactions.