1,3-Difunctionalization of β-Alkyl Nitroalkenes via Combination of Lewis Base Catalysis and Radical Oxidation

Wang, Ye; Zheng, Lei; Shi, Xiaodong; Chen, Yunfeng

1,3-Difunctionalization of β-Alkyl Nitroalkenes via Combination of Lewis Base Catalysis and Radical Oxidation

2021

Wang, Ye | Zheng, Lei | Shi, Xiaodong | Chen, Yunfeng

Upon treatment with a Lewis base catalyst, β-alkyl-substituted nitroalkenes could be readily converted into allylic nitro compounds. Examples of either C-1 or C-3 functionalization methods have been reported through nitro-elimination, giving alkene products. In this work, successful 1,3-difunctionalization was achieved through a synergetic Lewis base catalysis and TBHP radical oxidation, giving vinylic alkoxyamines in good to excellent yields. This work further extended the general synthetic application of β-alkyl nitroalkenes.

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