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Unclicking the click : metal-assisted mechanochemical cycloreversion of triazoles is possible.
Autorzy
Rok wydania
2017
Czasopismo
Angewandte Chemie - International Edition
Numer woluminu
56
Strony
7745-7749
DOI
10.1002/anie.201612507
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
The mechanochemical cycloreversion of 1,2,3-triazole compounds, which serve as unusually stable building blocks in materials and biomolecular chemistry as a result of mild "click chemistry", remains puzzling. We show that the hitherto discussed straight-forward retro-click mechanism of the 1,4-disubstituted isomer, even if CuI catalyzed, can be ruled out in view of more favorable activation free energies of destructive pathways. In stark contrast, the 1,5-regioiomer can undergo cycloreversion under rather mild mechanochemical conditions owing to its favorable response to the external force in conjunction with standard RuII catalysis.
Słowa kluczowe
click chemistry, computational chemistry, mechanochemistry, reaction mechanisms, triazole
Adres publiczny
http://dx.doi.org/10.1002/anie.201612507
Strona internetowa wydawcy
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