Direct C–H bond activation strategies enable rapid access to highly functionalized motifs from readily available, feedstock chemicals. In recent years, significant advances have been made in the field of transition metal-catalyzed C–H activation, however, achieving efficient and <i>regioselective </i>C–H functionalization still poses a major challenge. In 2015, the MacMillan group demonstrated that activation of strong α-hydroxy C–H bonds could be achieved via photoredox-mediated hydrogen atom transfer (HAT) using a transiently generated amine radical cation HAT catalyst. Through the merger of this C–H functionalization strategy with nickel catalysis, we have demonstrated that selective arylation of α-amino and α-oxy C–H bonds can be achieved. The catalytic protocol was applicable to the coupling of various electronically differentiated aryl bromides, including heteroaryl halide reaction partners, with a range of C–H nucleophiles.

C–H arylation via the merger of photoredox, hydrogen atom transfer and nickel catalysis

255th National Meeting (2018)

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