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A Site-Selective Amination Catalyst Discriminates Between Nearly Identical C-H Bonds of Unsymmetrical Disubstituted Alkenes
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
C−H activation reactions enable chemists to unveil new retrosynthetic disconnections and streamline
conventional synthetic approaches. A longstanding challenge in C−H activation is the inability to
distinguish electronically and sterically similar C–H bonds. Although numerous synergistic combinations
of transition-metal complexes and chelating directing groups have been utilized to distinguish C−H bonds,
undirected regioselective C−H functionalization strategies remain elusive. Herein, we report a
regioselective C−H activation/amination reaction of various unsymmetrical dialkyl-substituted alkenes.
The regioselectivity of C−H activation is correlated to the electronic properties of allylic C−H bonds
indicated by the corresponding 1JCH coupling constants. A linear relationship between the difference of
1JCH coupling constants of the two competing allylic C−H bonds (Δ
1JCH) and the C−H activation barriers (Δ
) has also been determined.