Herein,
we report a direct photochemical dehydrogenative C–N
coupling of unactivated C(sp2)–H and N(sp2)–H bonds. The catalysts or additive-free transformation of
2-([1,1′-biphenyl]-2-yl)-1H-benzo[d]imidazole to benzo[4,5]imidazo[1,2-f]phenanthridine
was achieved at ∼350 nm of irradiation via ε-hydrogen
abstraction. DFT calculations helped to understand that the N–H···π
interaction was essential for the reaction to proceed at a lower energy
than expected.
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