Metal-free nitrative cyclization of N-aryl imines with tert-butyl nitrite: dehydrogenative access to 3-nitroindoles.

Guo-Bo Deng, Jia-Ling Zhang, Yan-Yun Liu, Bang Liu, Xu-Heng Yang, Jin-Heng Li

Chemical communications (Cambridge, England) 2015 Feb 4

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We describe here a new metal-free route for the synthesis of 3-nitroindoles by the nitrative cyclization of N-aryl imines with tert-butyl nitrite. The radical transformation allows the assembly of the indole framework through oxidative cleavage of multi C-H bonds, a nitration, cyclization and isomerization cascade.

Citation

Guo-Bo Deng, Jia-Ling Zhang, Yan-Yun Liu, Bang Liu, Xu-Heng Yang, Jin-Heng Li. Metal-free nitrative cyclization of N-aryl imines with tert-butyl nitrite: dehydrogenative access to 3-nitroindoles. Chemical communications (Cambridge, England). 2015 Feb 4;51(10):1886-8