Redox-selective iron catalysis for α-amino C–H bond functionalization via aerobic oxidation
JY Hwang, AY Ji, SH Lee, EJ Kang - Organic letters, 2019 - ACS Publications
JY Hwang, AY Ji, SH Lee, EJ Kang
Organic letters, 2019•ACS PublicationsSingle-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) n 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 …
afford α-aminoalkyl radicals, which can be coupled with electrophilic partners to afford
various tetrahydroquinolines. Mechanistically, the Fe (phen) n 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 …
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)n2+/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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