Electrocatalytic oxidative C–H cycloamination towards tricyclic [1,2,4]triazolo-[3,4-i]purine nucleosides mediated by bromide ions
Qi-Liang Yang,
Wan-Wan Li,
Zhong-Xu Zhang
et al.
Abstract:A environmentally benign electrochemical approach is presented to access diversely functionalized [1,2,4]triazolo[3,4-i]purine heterocyclic framework. The bromide-mediated indirect oxidation strategy was utilized to promote intramolecular C(sp2)–H cycloamination in high efficiency and...
“…Therefore, we speculate that when n Bu 4 NBr is used in place of n Bu 4 NI, the reaction may follow the same pathway, with Br − serving a similar function as I − . 16 (For the possible explanations for the elimination of HI from 8a to yield 3a, see ESI §5.3 and §5.4. † The possible reaction mechanism with n Bu 4 NBr is shown in Fig.…”
Section: Organic and Biomolecular Chemistry Communicationmentioning
n
Bu4NI serves as both electrolyte and iodine mediator in the method, which is characterized by its simple operation (undivided electrolytic cells at room temperature), good atom efficiency, and eco-friendliness, with hydrogen as the sole byproduct.
“…Therefore, we speculate that when n Bu 4 NBr is used in place of n Bu 4 NI, the reaction may follow the same pathway, with Br − serving a similar function as I − . 16 (For the possible explanations for the elimination of HI from 8a to yield 3a, see ESI §5.3 and §5.4. † The possible reaction mechanism with n Bu 4 NBr is shown in Fig.…”
Section: Organic and Biomolecular Chemistry Communicationmentioning
n
Bu4NI serves as both electrolyte and iodine mediator in the method, which is characterized by its simple operation (undivided electrolytic cells at room temperature), good atom efficiency, and eco-friendliness, with hydrogen as the sole byproduct.
Electrosynthesis of selenylated‐oxazolone derivatives via cascade selenylation/cyclization of ynamides was disclosed. A series of diaryl diselenides, dialkyl diselenides, and heteroaryl‐substituted ynamides was tolerated in this protocol and delivered 4‐selenyloxazolones in 28‐83% yield. The scale‐up reaction and the oxidation of selenylated‐oxazolones was performed to showcase the practicability of this method. Furthermore, mechanistic experiments indicated that a cationic pathway instead of aradical pathway was probably involved.
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