Radical Borylative Cyclization of Isocyanoarenes with N-Heterocyclic Carbene Borane: Synthesis of Borylated Aza-arenes

Borylated aza-arenes are of great importance in the area of organic synthesis. A radical borylative cyclization of isocyanoarenes with N-heterocyclic carbene borane (NHC-BH3) under metal-free conditions was developed. The reaction allows the efficient assembly of several types of borylated aza-arenes (phenanthridines, benzothiazoles, etc.), which are difficult to access using alternative methods. Mild reaction conditions, a good functional-group tolerance, and generally good efficiencies were observed. The utility of these products is demonstrated, and the mechanism is discussed.

Automated summary

A radical borylative cyclization method under metal-free conditions was developed for the efficient assembly of various types of borylated aza-arenes. The reaction exhibited mild conditions, good functional-group tolerance, and generally good efficiencies. The utility of the products was demonstrated, and the mechanism was discussed.