Chemistry - An Asian Journal p. 380 - 390 (2020)
Update date:2022-08-31
Topics:
Liu, Peiye
Brassard, Christopher J.
Lee, Justin P.
Zhu, Lei
In an alcoholic solvent under the catalysis of Cu(OAc)2?H2O, organic azide and terminal alkyne could oxidatively couple to afford 5-alkynyl-1,2,3-triazole (alkynyltriazole) at room temperature under an atmosphere of O2 in a few hours. The involvement of 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) is essential, without which the redox neutral coupling instead proceeds to produce 5-H-1,2,3-triazole (protiotriazole) as the major product. Therefore, DBN switches the redox neutral coupling between terminal alkyne and organic azide, the copper-catalyzed “click” reaction to afford protiotriazole, to an oxidation reaction that results in alkynyltriazole. The organic base DBN is effective in accelerating the copper(II)-catalyzed oxidation of terminal alkyne or copper(I) acetylide, which is intercepted by an organic azide to produce alkynyltriazole. The proposed mechanistic model suggests that the selectivity between alkynyl- and protiotriazole, and other acetylide or triazolide oxidation products is determined by the competition between copper(I)-catalyzed redox neutral cycloaddition and copper(II)/O2-mediated acetylide oxidation after the formation of copper(I) acetylide.
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Doi:10.1016/S0022-328X(00)89280-3
(1975)Doi:10.1002/chem.202003521
(2020)Doi:10.1039/c4cy00996g
(2015)Doi:10.1021/ja01650a043
(1954)Doi:10.1002/chem.201404398
(2014)Doi:10.1016/j.bmcl.2008.08.024
(2008)