Beilstein J. Org. Chem.2021,17, 1600–1628, doi:10.3762/bjoc.17.114
such as cinnamyl, (ethoxycarbonyl)methyl, 1-naphthalenemethyl, and (phenylthio)methyl were cyclized with ethynylstibanes 82 and diaryl diselenides 84 to afford the desired triazole products. The reaction between ethynylstibane, organic azide, and a range of diaryl diselenides 84 including sterically
hindered o-substituted and heterocyclic derivatives efficiently proceeded to give the desired 5-selanyl-1,2,3-triazoles 85 [53].
A possible mechanism was suggested and is displayed in Scheme 26. First, the Cu(I)-catalyzed cyclization of ethynylstibane 82 and azide 83 gives the intermediate 86, which
PDF
Graphical Abstract
Figure 1:
Some significant triazole derivatives [8,23-27].
Beilstein J. Org. Chem.2016,12, 1309–1313, doi:10.3762/bjoc.12.123
] cycloaddition of a ethynylstibane with organic azides in the presence of CuBr (5 mol %) under aerobic conditions. The reaction of 5-stibanotriazole with HCl, I2, and NOBF4 afforded 1-benzyl-4-phenyltriazole, 1-benzyl-5-iodo-4-phenyltriazole, and a pentavalent organoantimony compound, respectively.
Keywords
: cycloaddition; copper catalyst; ethynylstibane; organic azide; 1,2,3-triazole; Introduction
The 1,3-dipolar azide–alkyne cycloaddition (AAC) has been effective for the synthesis of a wide variety of 1,2,3-triazoles [1]. However, this reaction has some limitations such as the requirement of high temperature and
recovered (84%). These two experiments indicate that the formation of 5-H-triazole 4 progresses via 5-stibanotriazole 3a, the cycloaddition product of 1 with 2a.
To investigate the scope and limitations of the CuAAC reaction of stibane, ethynylstibane 1 was reacted with a series of organic azides 2 under
PDF
Graphical Abstract
Scheme 1:
Copper-catalyzed [3 + 2] cycloaddition of 1 with organic azides 2. Reaction conditions: 1 (0.5 mmol...