Cationic 1,2,3-Triazolium Alkynes: Components To Enhance 1,4-Regioselective Azide–Alkyne Cycloaddition Reactions
| Autor: | Jesus M. Aizpurua, José I. Miranda, Maialen Sagartzazu-Aizpurua, Yuri Reyes, Zaira Monasterio |
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| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Cationic polymerization Alkyne Regioselectivity 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry Combinatorial chemistry Cycloaddition Transition state 0104 chemical sciences chemistry.chemical_compound Azide Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 18:788-791 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | 4-Alkynyl-1,2,3-triazolium cations undergo thermal [3 + 2] cycloaddition reactions with azides roughly 50- to 100-fold faster than comparable noncharged alkynes. Further, the reaction is highly 1,4-regioselective (dr up to 99:1) owing to the selective stabilization of 1,4-TS transition states via conjugative π-acceptor assistance of the alkyne triazolium ring. The novel cationic triazolium alkynes also accelerate the CuAAC reaction to provide bis(1,2,3-triazoles) in an “ultrafast” way ( |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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