108306-81-6Relevant articles and documents
Flavin Nitroalkane Oxidase Mimics Compatibility with NOx/TEMPO Catalysis: Aerobic Oxidization of Alcohols, Diols, and Ethers
Thapa, Pawan,Hazoor, Shan,Chouhan, Bikash,Vuong, Thanh Thuy,Foss, Frank W.
, p. 9096 - 9105 (2020/08/14)
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.
Chemoselective Oxidation of the Primary Alcohol Function of Diols Catalyzed by Zirconocene Complexes
Nakano, Tatsuya,Terada, Takanobu,Ishii, Yasutaka,Ogawa, Masaya
, p. 774 - 776 (2007/10/02)
Zirconocene complexes, Cp2ZrH2 and Cp2Zr2, catalyze the Oppenauer-type oxidation of alcohol functions to the corresponding carbonyl compounds in the presence of an appropriate hydrogen acceptor such as benzophenone.In the oxidation of primary α,ω-diols and of diols containing two secondary alcohol functions, one of the alcohol functions is selectively oxidized to form hydroxy aldehydes and hydroxy ketones, respectively, in substantial yields.The chemoselective oxidation of the primary alcohol function can be achieved in the oxidation of diols containing both the primary and secondary alcohol functions.
