Department of Chemistry and Biochemistry, The University of Texas at Arlington, 700 Planetarium Place, Arlington, Texas 76019, USA.
Org Lett. 2012 Oct 5;14(19):5150-3. doi: 10.1021/ol302479b. Epub 2012 Sep 27.
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 O(2) or air as the stoichiometric oxidant source.
首次报道了以分子氧作为末端氧化剂的 Dakin 氧化反应。受天然酶促氧化还原体系中黄素和 NAD(P)H 辅酶的启发，使用黄素有机催化剂和 Hantzsch 酯实现了无过渡金属的有氧氧化反应。儿茶酚和富电子苯酚的反应仅需 0.1mol%的催化剂用量、1当量的 Hantzsch 酯和 O(2)或空气作为化学计量氧化剂。
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