Regioselective Zn(OAc)2-catalyzed azide–alkyne cycloaddition in water: the green click-chemistry

Bibliographic Details
Parent link:Organic Chemistry Frontiers
Vol. 4, iss. 6.— 2017.— [P. 978-985]
Corporate Authors: Национальный исследовательский Томский политехнический университет (ТПУ) Институт физики высоких технологий (ИФВТ) Кафедра биотехнологии и органической химии (БИОХ), Национальный исследовательский Томский политехнический университет (ТПУ) Институт природных ресурсов (ИПР) Кафедра технологии органических веществ и полимерных материалов (ТОВПМ)
Other Authors: Morozova M. A. Mariya Aleksandrovna, Yusubov M. S. Mekhman Suleiman-Ogly (Suleimanovich), Kratochvil B. Bogumil, Eigner V., Bondarev A. A. Aleksandr Aleksandrovich, Yoshimura A. Akira, Saito A. Akio, Zhdankin V. V. Viktor Vladimirovich, Trusova M. E. Marina Evgenievna, Postnikov P. S. Pavel Sergeevich
Summary:Title screen
A new method of azide–alkyne cycloaddition (AAC) in the presence of Zn(OAc)2 as an inexpensive and environmentally friendly catalyst in neat water has been developed. The proposed methodology has been applied for the synthesis of 1,4-disubstituted-1,2,3-triazoles from terminal alkynes and 1,4,5-trisubstituted-1,2,3-triazoles from internal alkynes. It has been found that Zn-catalyzed AAC is extremely sensitive to steric hindrance in acetylenes and a method of regioselective triazole ring formation has been proposed. Particularly important is the isolation and characterization of a relatively stable Zn-containing intermediate, which has been characterized by NMR and HRMS.
Режим доступа: по договору с организацией-держателем ресурса
Language:English
Published: 2017
Subjects:
Online Access:https://doi.org/10.1039/C6QO00787B
Format: Electronic Book Chapter
KOHA link:https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=655881