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Flavin Nitroalkane Oxidase Mimics Compatibility with NOx/TEMPO Catalysis: Aerobic Oxidization of Alcohols, Diols, and Ethers

التفاصيل البيبلوغرافية
العنوان: Flavin Nitroalkane Oxidase Mimics Compatibility with NOx/TEMPO Catalysis: Aerobic Oxidization of Alcohols, Diols, and Ethers
المؤلفون: Thanh Thuy Vuong, Frank W. Foss, Shan Hazoor, P. Thapa, Bikash Chouhan
المصدر: The Journal of Organic Chemistry. 85:9096-9105
بيانات النشر: American Chemical Society (ACS), 2020.
سنة النشر: 2020
مصطلحات موضوعية: inorganic chemicals, biology, 010405 organic chemistry, Organic Chemistry, Formaldehyde, Flavoprotein, Sulfoxide, Flavin group, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, chemistry, Nitroalkane oxidase, biology.protein, Organic chemistry, Selectivity, NOx
الوصف: Biomimetic flavin organocatalysts oxidize nitromethane to formaldehyde and NOx-providing a relatively nontoxic, noncaustic, and inexpensive source for catalytic NO2 for aerobic TEMPO oxidations of alcohols, diols, and ethers. Alcohols were oxidized to aldehydes or ketones, cyclic ethers to esters, and terminal diols to lactones. In situ trapping of NOx and formaldehyde suggest an oxidative Nef process reminiscent of flavoprotein nitroalkane oxidase reactivity, which is achieved by relatively stable 1,10-bridged flavins. The metal-free flavin/NOx/TEMPO catalytic cycles are uniquely compatible, especially compared to other Nef and NOx-generating processes, and reveal selectivity over flavin-catalyzed sulfoxide formation. Aliphatic ethers were oxidized by this method, as demonstrated by the conversion of (-)-ambroxide to (+)-sclareolide.
تدمد: 1520-6904
0022-3263
URL الوصول: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::cf7e09eede800151d56ab0b772c01b31
https://doi.org/10.1021/acs.joc.0c01013
حقوق: CLOSED
رقم الأكسشن: edsair.doi.dedup.....cf7e09eede800151d56ab0b772c01b31
قاعدة البيانات: OpenAIRE
الوصف
تدمد:15206904
00223263