Triiodide-Mediated δ-Amination of Secondary C–H Bonds

A recent article published by the group of Professor David Nagib and his group from The Ohio State University (USA) describes a highly innovative chemical method that enables the δ-amination of secondary C–H bonds within a large range of unactivated amines bearing biologically relevant functionalities. Although the century-old Hofmann–Löffler–Freytag (HLF) reaction has been developed to solve this synthetic challenge in the context of biased amines containing weak C–H bonds (e.g. tertiary, benzylic, α-oxy), a solution does not yet exist for applying this approach to the δ-selective amination of secondary C–H bonds. 

In this manuscript, the authors present a new strategy in which I2 is prepared in situ from NaI and rapidly trapped as a triiodide (I3–) species. By sequestering the necessary I2 as I3–, they demonstrate that this new triiodide strategy can solve the ongoing synthetic challenge of δ-amination of unactivated, secondary C–H bonds.

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