Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO <sub>2</sub>
Akira Shiozuka, Kohei Sekine, Yoichiro Kuninobu
Abstract
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 (B2pin2) 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.
Topics & Concepts
ChemistryBorylationYield (engineering)PhotochemistryBond cleavageCleavage (geology)PyreneCatalysisMedicinal chemistryOrganic chemistryCombinatorial chemistryArylMaterials scienceGeotechnical engineeringAlkylMetallurgyFracture (geology)EngineeringOrganoboron and organosilicon chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions