Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO2

Herein, direct unreactive C-N borylation of aromatic amines by a photocatalyst was achieved. The C-N borylation of aromatic amines with bis(pinacolato)diboron (B(2)pin(2)) proceeded using a pyrene catalyst under light irradiation to afford desired borylated products and aminoborane as a byproduct. The yield of the borylated product improved under a CO2 atmosphere which probably reduced the inhibitory effect of aminoborane. Mechanistic studies suggested that the C-N bond cleavage and C-B bond formation proceeded via a concerted pathway.

Automated summary

Direct unreactive C-N borylation of aromatic amines was achieved using a photocatalyst, with improved yield of borylated products under a CO2 atmosphere, suggesting a possible mechanism involving C-N bond cleavage and C-B bond formation via a concerted pathway.