Fluoroamide-Directed Regiodivergent C-Alkylation of Nitroalkanes
Zhibin Du1, Shiwen Liu2, Yuke Li3
1School of Chemistry and Chemical Engineering, Nanchang University, Nanchang, Jiangxi 330031, China.
Abstract:
Herein, by exploiting different activation modes of fluoroamides, we achieved α- and δ-C(sp3)-H alkylation of nitroalkanes with switchable regioselectivity. Cu catalysis enabled the interception of a distal C-centered radical by a N-centered radical to couple nitroalkanes and unactivated δ-C-H bonds. In addition, imines generated in situ by fluoroamides were trapped by nitroalkanes to realize the α-C-H alkylation of amides. Both of those scalable protocols have broad substrate scopes and good functional group tolerance.
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