Modular Synthesis of Polycarbonyl Compounds via Regioselective Hydration of Oxo-Alkynes.

Autor: Zhou M; Key Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, P. R. China., Zhao DR; Key Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, P. R. China., Zhang L; Key Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, P. R. China., Kuang YJ; Key Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, P. R. China., Zhao YJ; Key Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, P. R. China., Yu Y; Key Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, P. R. China., Luo QL; Key Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, P. R. China.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2024 Nov 15; Vol. 89 (22), pp. 16917-16922. Date of Electronic Publication: 2024 Nov 02.
DOI: 10.1021/acs.joc.4c01550
Abstrakt: A novel protocol has been developed for the modular synthesis of polycarbonyl compounds by catalytic hydration of 1,3-diketone-tethered alkynes. The hydration process exhibits good regioselectivity and high yields at room temperature, avoiding the use of strong acids and noble metals and the requirement for elevated temperatures. Mechanistic insights suggest that the hydration proceeds through a concerted process of alkyne protonation and remote carbonyl participation. This approach provides direct access to tandem heterocycle dyads and triads.
Databáze: MEDLINE
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