1588517-25-2Relevant articles and documents
Native functionality in triple catalytic cross-coupling: sp3 C-H bonds as latent nucleophiles
Shaw, Megan H.,Shurtleff, Valerie W.,Terrett, Jack A.,Cuthbertson, James D.,MacMillan, David W.C.
, p. 1304 - 1308 (2016)
The use of sp3 C-H bonds - which are ubiquitous in organic molecules - as latent nucleophile equivalents for transition metal - catalyzed cross-coupling reactions has the potential to substantially streamline synthetic efforts in organic chemistry while bypassing substrate activation steps. Through the combination of photoredox-mediated hydrogen atom transfer (HAT) and nickel catalysis, we have developed a highly selective and general C-H arylation protocol that activates a wide array of C-H bonds as native functional handles for cross-coupling. This mild approach takes advantage of a tunable HAT catalyst that exhibits predictable reactivity patterns based on enthalpic and bond polarity considerations to selectively functionalize α-amino and α-oxy sp3 C-H bonds in both cyclic and acyclic systems.
