《Taming Ambident Triazole Anions: Regioselective Ion Pairing Catalyzes Direct N-Alkylation with Atypical Regioselectivity》 was written by Dale, Harvey J. A.; Hodges, George R.; Lloyd-Jones, Guy C.. COA of Formula: C2H3N3This research focused ontriazole regioselective alkylation organocatalysis ion pairing. The article conveys some information:
Controlling the regioselectivity of ambident nucleophiles toward alkylating agents is a fundamental problem in heterocyclic chem. Unsubstituted triazoles are particularly challenging, often requiring inefficient stepwise protection-deprotection strategies and prefunctionalization protocols. Herein we report on the alkylation of archetypal ambident 1,2,4-triazole, 1,2,3-triazole, and their anions, analyzed by in situ 1H/19F NMR, kinetic modeling, diffusion-ordered NMR spectroscopy, X-ray crystallog., highly correlated coupled-cluster computations [CCSD(T)-F12, DF-LCCSD(T)-F12, DLPNO-CCSD(T)], and Marcus theory. The resulting mechanistic insights allow design of an organocatalytic methodol. for ambident control in the direct N-alkylation of unsubstituted triazole anions. Amidinium and guanidinium receptors are shown to act as strongly coordinating phase-transfer organocatalysts, shuttling triazolate anions into solution The intimate ion pairs formed in solution retain the reactivity of liberated triazole anions but, by virtue of highly regioselective ion pairing, exhibit alkylation selectivities that are completely inverted (1,2,4-triazole) or substantially enhanced (1,2,3-triazole) compared to the parent anions. The methodol. allows direct access to 4-alkyl-1,2,4-triazoles (rr up to 94:6) and 1-alkyl-1,2,3-triazoles (rr up to 99:1) in one step. Regioselective ion pairing acts in effect as a noncovalent in situ protection mechanism, a concept that may have broader application in the control of ambident systems. In the part of experimental materials, we found many familiar compounds, such as 1H-1,2,3-Triazole(cas: 288-36-8COA of Formula: C2H3N3)
1H-1,2,3-Triazole(cas: 288-36-8) belongs to triazoles. Triazoles are an important group of nitrogen-containing five-membered heterocyclic scaffolds. Triazoles are core structures of several drugs and pharmaceutical agents. Triazole derivatives possess antimicrobial, antiparasitic, antidiabetic, analgesic, and anti-inflammatory properties COA of Formula: C2H3N3
Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics