Xiang-Chuang Tan, Lei Yan, Hao-Ni Qin and Peng-Fei Xu*
https://doi.org/10.1039/D5GC03425F
Abstract
Herein, we report the development of a carbon-bound radical cyanating reagent, 2-methyl-2-(pyridin-2 yl)malononitrile (MPYMN), which enables metal-free photocatalytic cyanation with high reactivity and site selectivity. MPYMN is a bench-stable, readily accessible solid that does not release cyanide during reac tions nor does it require metals or harsh conditions. It exhibits superior performance compared to com mercially available cyanating agents and other carbon-bound cyanide sources. Importantly, the steric effect of the quaternary carbon in MPYMN facilitates reagent-controlled site-selective cyanation. The syn thetic utility of this reagent is demonstrated by its compatibility with both photoredox and hydrogen atom transfer (HAT) processes, including efficient late-stage functionalization of complex molecules relevant to medicinal chemistry.