Department of Chemistry and Biochemistry , University of California , Santa Barbara , California 93106 , United States.
Facultad de Química, Departamento de Farmacia , Universidad Nacional Autónoma de México, CDMX , Mexico City 04510 , México.
Org Lett. 2018 Sep 7;20(17):5094-5097. doi: 10.1021/acs.orglett.8b01883. Epub 2018 Aug 13.
A copper-catalyzed oxidative cleavage of electron-rich olefins into their corresponding carbonyl derivatives is described as an alternative to ozonolysis. The scope includes various precursors to aryl ketone derivatives, as well as oxidations of enol ethers bearing atypical alkyl and dialkyl substitution, the first of their kind among such metal catalyzed alkene cleavage reactions. The use of an inexpensive copper salt, room temperature conditions, an aerobic atmosphere, and water as the global reaction medium highlight the green features of this new method. Associated mechanistic investigations are also presented.
描述了一种铜催化的富电子烯烃的氧化裂解反应，可作为臭氧化反应的替代方法。该反应的范围包括各种芳基酮衍生物的前体，以及带有非典型烷基和二烷基取代基的烯醇醚的氧化，这是此类金属催化的烯烃裂解反应中首例。该方法使用廉价的铜盐、室温条件、有氧气氛和水作为全球反应介质，突出了这种新方法的绿色特点。还提出了相关的机理研究。
