Organocatalytic cascade aldimine condensation/[1,6]-hydride transfer/Mannich-type cyclization: sustainable access to indole-2,3-fused diazocanes An unprecedented organocatalytic cascade aldimine condensation/[1,6]-hydride transfer/Mannich-type cyclization of indole-2-carbaldehydes with o-aminoanilines was developed to assemble polycyclic indole-2,3-fused diazocanes in one-step. This novel methodology features high step- and atom-economy, redox-neutral, metal free and room temperature.