A rhodium‐catalyzed cascade cross‐coupling/spirocyclization/formal [4+2] cycloaddition reaction of 3‐(2‐isocyanoethyl)indoles with aromatic azides is developed, providing a general synthetic protocol to polycyclic spiroindolines bearing a pentasubstituted guanidine moiety with moderate to excellent yields. This transformation is highly effective since one C−C, one C=N, three C−N bonds as well as two new rings are constructed in a single step. More importantly, this work represents a new reactivity pattern of 3‐(2‐isocyanoethyl)indole, and thus constitutes an valuable addition to 3‐(2‐isocyanoethyl)indole chemistry.

A base-catalyzed divergent synthesis of multisubstituted imidazoles through TosMIC-based [3 + 2] cyclization reaction has been developed. In the presence of ketenimines and tBuONa, 1,4,5-trisubstituted imidazoles were obtained. Nonetheless, in...

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Catalytic functionalization of indoles has been one of the most flourishing topics in organic chemistry. However, most known methods for the synthetic modifications of indoles take place at the C3...