A diversity-oriented sequential <i>C</i>-arylation of 7-azaindoles is reported herein, which avoids a de-novo approach. A tri-halogenated 7-azaindole precursor was used for three chemo-selective Suzuki-Miyaura cross-coupling reactions and a C-H arylation, i.e. C3→C5→C6→C2 using common Pd catalysts. Ligands, solvents and temperature control were important factors in optimizing selectivity. This multi-step scheme furnished sterically hindered triaryl and tetraaryl derivatives in good to excellent yields. The tetraaryl 7-azaindoles showed aggregation-induced emission profiles, which can be modulated using different aryl groups. A substituent dependent study can thus be advantageous in developing specific AIEgens for material applications.

Pd catalyzed sequential <i>C</i>-arylation of 7-azaindoles: Introducing tetra-aryl 7-azaindoles as AIEgens

ACS Fall 2021

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Pd catalyzed sequential C-arylation of 7-azaindoles: Introducing tetra-aryl 7-azaindoles as AIEgens