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Radical ipso-Substitution of a Carbon–Fluorine Bond Leading to Fluoro-7-azaindolines and Fluoro-7-azaindoles

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journal contribution
posted on 16.05.2014, 00:00 by Zhibo Liu, Ling Qin, Samir Z. Zard
Rare examples of a synthetically useful radical ipso-substitution of a carbon–fluorine bond are reported, leading to highly functionalized 5,6-difluoro-7-azaindolines. An unexpected hydrogen atom translocation and fragmentation with loss of molecular nitrogen and formation of a nitrile were observed in the case of an N-benzyl-tetrazole derivative.