Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Dibenziodolium and diphenyliodonium triflates display high catalytic activity for the multicomponent reaction that leads to a series of imidazopyridines. Density functional theory (DFT) calculations indicate that both the salts can play the role of hybrid hydrogen- and halogen-bond-donating organocatalysts, which electrophilically activate the carbonyl and imine groups during the reaction process. The ortho-H atoms in the vicinal position to the I atom play a dual role: forming additional noncovalent bonds with the ligated substrate and increasing the maximum electrostatic potential on the σ-hole at the iodine atom owing to the effects of polarization. Dibenziodolium triflate exhibits higher catalytic activity, and the results obtained from 1H nuclear magnetic resonance (NMR) titrations, in conjunction with those from DFT calculations, indicate that this could be explained in terms of the additional energy required for the rotation of the phenyl ring in the diphenyliodonium cation during ligation of the substrate.
Переведенное название | Соли диарилиодония в качестве гибридных органокатализаторов — доноров водородной и галогенной связи для реакции Грёбке—Блэкбёрна—Бьенаме |
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Язык оригинала | английский |
Страницы (с-по) | 4569-4579 |
Число страниц | 11 |
Журнал | The Journal of organic chemistry |
Том | 87 |
Номер выпуска | 7 |
Дата раннего онлайн-доступа | 17 фев 2022 |
DOI | |
Состояние | Опубликовано - 1 апр 2022 |
ID: 92927402