Aerobic organocatalytic oxidation of aryl aldehydes: flavin catalyst turnover by Hantzsch's ester
S Chen, FW Foss Jr - Organic letters, 2012 - ACS Publications
Organic letters, 2012•ACS Publications
The first Dakin oxidation fueled by molecular oxygen as the terminal oxidant is reported.
Flavin and NAD (P) H coenzymes, from natural enzymatic redox systems, inspired the use of
flavin organocatalysts and a Hantzsch ester to perform transition-metal-free, aerobic
oxidations. Catechols and electron-rich phenols are achieved with as low as a 0.1 mol%
catalyst loading, 1 equiv of Hantzsch ester, and O2 or air as the stoichiometric oxidant
source.
Flavin and NAD (P) H coenzymes, from natural enzymatic redox systems, inspired the use of
flavin organocatalysts and a Hantzsch ester to perform transition-metal-free, aerobic
oxidations. Catechols and electron-rich phenols are achieved with as low as a 0.1 mol%
catalyst loading, 1 equiv of Hantzsch ester, and O2 or air as the stoichiometric oxidant
source.
The first Dakin oxidation fueled by molecular oxygen as the terminal oxidant is reported. Flavin and NAD(P)H coenzymes, from natural enzymatic redox systems, inspired the use of flavin organocatalysts and a Hantzsch ester to perform transition-metal-free, aerobic oxidations. Catechols and electron-rich phenols are achieved with as low as a 0.1 mol % catalyst loading, 1 equiv of Hantzsch ester, and O2 or air as the stoichiometric oxidant source.
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