| Autor: |
Dubovtsev AY; Saint Petersburg State University , Universitetskaya Nab. 7/9 , 199034 Saint Petersburg , Russian Federation., Shcherbakov NV; Saint Petersburg State University , Universitetskaya Nab. 7/9 , 199034 Saint Petersburg , Russian Federation., Dar'in DV; Saint Petersburg State University , Universitetskaya Nab. 7/9 , 199034 Saint Petersburg , Russian Federation., Kukushkin VY; Saint Petersburg State University , Universitetskaya Nab. 7/9 , 199034 Saint Petersburg , Russian Federation. |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2020 Jan 17; Vol. 85 (2), pp. 745-757. Date of Electronic Publication: 2019 Dec 31. |
| DOI: |
10.1021/acs.joc.9b02785 |
| Abstrakt: |
2,3-Dichloropyridine N -oxide, a novel oxygen transfer reagent, allows the conductance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid additives and under mild conditions to furnish the target species, including those derivatized by highly acid-sensitive groups. The developed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even unsubstituted acetylene (40 examples; yields up to 99%). The oxidation was successfully integrated into the trapping of reactive dicarbonyls by one-pot heterocyclization and into the synthesis of six-membered azaheterocycles. This synthetic acid-free route was also successfully applied for the total synthesis of a natural 1,2-diketone. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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