Redox-Selective Iron Catalysis for α-Amino C-H Bond Functionalization via Aerobic Oxidation
Joon Young Hwang1, A Young Ji1, Sang Hyeok Lee1
1Department of Applied Chemistry , Kyung Hee University , Yongin 17104 , Korea.
Abstract:
Single-electron oxidation and α-deprotonation of tertiary anilines using Fe(phen)3(PF6)3 afford α-aminoalkyl radicals, which can be coupled with electrophilic partners to afford various tetrahydroquinolines. Mechanistically, the Fe(phen)2+/3+ catalytic cycle is maintained by O2 or a TBHP oxidant, and the presence of the oxygen bound iron complex, Fe(III)-OO(H), was elucidated by electron paramagnetic resonance and electrospray ionization mass spectrometry. This redox-selective nonheme iron catalyst behaves similarly to bioinspired heme iron catalysts.
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