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- W4235655389 abstract "Abstract Methyl‐selective α‐oxygenation of tertiary amines is a highly attractive approach for synthesizing formamides while preserving the amine substrate skeletons. Therefore, the development of efficient catalysts that can advance regioselective α‐oxygenation at the N ‐methyl positions using molecular oxygen (O 2 ) as the terminal oxidant is an important subject. In this study, we successfully developed a highly regioselective and efficient aerobic methyl‐selective α‐oxygenation of tertiary amines by employing a Cu/nitroxyl radical catalyst system. The use of moderately hindered nitroxyl radicals, such as 1,5‐dimethyl‐9‐azanoradamantane N ‐oxyl (DMN‐AZADO) and 1‐methyl‐2‐azaadamanane N ‐oxyl (1‐Me‐AZADO), was very important to promote the oxygenation effectively mainly because these N ‐oxyls have longer life‐times than less hindered N ‐oxyls. Various types of tertiary N ‐methylamines were selectively converted to the corresponding formamides. A plausible reaction mechanism is also discussed on the basis of experimental evidence, together with DFT calculations. The high regioselectivity of this catalyst system stems from steric restriction of the amine‐ N ‐oxyl interactions." @default.
- W4235655389 created "2022-05-12" @default.
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- W4235655389 date "2019-10-04" @default.
- W4235655389 modified "2023-10-13" @default.
- W4235655389 title "Methyl‐Selective α‐Oxygenation of Tertiary Amines to Formamides by Employing Copper/Moderately Hindered Nitroxyl Radical (DMN‐AZADO or 1‐Me‐AZADO)" @default.
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- W4235655389 doi "https://doi.org/10.1002/ange.201909005" @default.
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