Premium
Instantaneous Click Chemistry by a Copper‐Containing Polymeric‐Membrane‐Installed Microflow Catalytic Reactor
Author(s) -
Yamada Yoichi M. A.,
Ohno Aya,
Sato Takuma,
Uozumi Yasuhiro
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503178
Subject(s) - cycloaddition , click chemistry , chemistry , copper , alkyne , catalysis , azide , inorganic chemistry , polymer chemistry , organic chemistry
The copper(I)‐catalyzed Huisgen cycloaddition (azide–alkyne cycloaddition) is an important reaction in click chemistry that ideally proceeds instantaneously. An instantaneous Huisgen cycloaddition has been developed that uses a novel catalytic dinuclear copper complex‐containing polymeric membrane‐installed microflow device. A polymeric membranous copper catalyst was prepared from poly(4‐vinylpyridine), copper(II) sulfate, sodium chloride, and sodium ascorbate at the interface of two laminar flows inside microchannels. Elucidation of the structure by XANES, EXAFS, and elemental analysis, as well as second‐order Møller–Plesset perturbation theory (MP2) calculations and density functional theory (DFT) calculations assigned the local structure near Cu as a μ‐chloro dinuclear Cu I complex. The microflow device promotes the instantaneous click reaction of a variety of alkynes and organic azides to afford the corresponding triazoles in quantitative yield.