4.8 Article

Anaerobic Nitroxide-Catalyzed Oxidation of Alcohols Using the NO+/NO• Redox Pair

Journal

ORGANIC LETTERS
Volume 16, Issue 1, Pages 58-61

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol403016p

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Funding

  1. grant agency of the Czech Republic [13-40188S]
  2. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic [RVO: 61388963]
  3. Gilead Sciences & IOCB research center

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A new method for alcohol oxidation using TEMPO or AZADO in conjunction with BF3 center dot OEt2 or LiBF4 as precatalysts and tert-butyl nitrite as a stoichiometric oxidant has been developed. The system is based on a NO+/NO center dot pair for nitroxide reoxidation under anaerobic conditions. This allows the simple, high-yielding conversion of various achiral and chiral alcohols to carbonyl compounds without epimerization and no formation of nonvolatile byproducts.

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