Three-Component Reactions of α-CF3 Carbonyls, NaN3, and Amines for the Synthesis of NH-1,2,3-Triazoles
| Autor: | Leiyang Lv, Zhiping Li, Ge Gao, Kuantao Mao, Yani Luo |
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| Rok vydání: | 2021 |
| Předmět: | |
| Zdroj: | The Journal of Organic Chemistry. 86:17197-17212 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.1c02288 |
| Popis: | The development of methods for the assembly of 1,2,3-triazoles is an important topic due to the broad applications of this motif in various scientific fields. In this work, we demonstrate that the three-component assembly of α-CF3 carbonyls, NaN3, and amines was achieved for the selective construction of a variety of 5-amino NH-1,2,3-triazoles under transition-metal-free and open-air conditions. The method provides a general and operationally simple route to functionalized biologically important molecules including carbohydrates, nucleosides, and peptides and exhibits broad substrate scopes. We further demonstrate that the NH-1,2,3-triazoles can be smoothly converted to the regiospecific N-2 alkylated 1,2,3-triazole products. Mechanistic studies based on experiments and density functional theory calculations showed that this transformation proceeds via defluorination-initiated programmed substitution/cyclization/H-transfer to give the 4,5-difunctionalized captodative NH-1,2,3-triazole product. |
| Databáze: | OpenAIRE |
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