《Site-selective α-C-H Functionalization of Trialkylamines via Reversible HAT-Catalysis》 was written by Shen, Yangyang; Funez-Ardoiz, Ignacio; Schoenebeck, Franziska; Rovis, Tomislav. Formula: C6H11NOThis research focused ontrialkylamine regioselective functionalization reversible HAT catalysis. The article conveys some information:
Despite the recent breakthrough of catalytic alkylation of dialkylamines, the selective α-C(sp3)-H bond functionalization of widely available trialkylamine scaffolds holds promise to streamline complex trialkylamine synthesis, accelerate drug discovery and execute late-stage pharmaceutical modification with complementary reactivity. However, the canonical methods always result in functionalization at the less-crowded site. Herein, authors describe a solution to switch the reaction site through fundamentally overcoming the steric control that dominates such processes. By rapidly establishing an equilibrium between α-amino C(sp3)-H bonds and a highly electrophilic thiol radical via reversible hydrogen atom transfer, authors leverage a slower radical-trapping step with electron-deficient olefins to selectively forge a C(sp3)-C(sp3) bond with the more-crowded α-amino radical, with the overall selectivity guided by Curtin-Hammett principle. This subtle reaction profile has unlocked a new strategic concept in direct C-H functionalization arena for forging C-C bonds from a diverse set of trialkylamines with high levels of site-selectivity and preparative utility. The broad consequences of this dynamic system, together with the ability to forge N-substituted quaternary carbon centers and implement late-stage functionalization techniques, holds potential to streamline complex trialkylamine synthesis and accelerate small-mol. drug discovery. In the experiment, the researchers used 1-Methyl-4-piperidone(cas: 1445-73-4Formula: C6H11NO)
1-Methyl-4-piperidone(cas: 1445-73-4) is a member of piperidine. Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of biological activities. Hence, continuous efforts have been made to develop convenient methods to prepare piperidine derivatives.Formula: C6H11NO
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem