Mechanochemical Synthesis of Silylcyclopentenes via Ball Milling.

Autor: Gao P; School of Chemistry and Chemical Engineering, Yangzhou University, Siwangting Road 180, 225002, Yangzhou, P. R. China., Li Y; School of Chemistry and Chemical Engineering, Yangzhou University, Siwangting Road 180, 225002, Yangzhou, P. R. China., Zhang D; Medicine Centre, Guangxi University of Science and Technology, Liushi Road 257, Liuzhou, Guangxi, 545006, P. R. China., Zhang G; School of Chemistry and Chemical Engineering, Yangzhou University, Siwangting Road 180, 225002, Yangzhou, P. R. China., Gao L; School of Chemistry and Chemical Engineering, Yangzhou University, Siwangting Road 180, 225002, Yangzhou, P. R. China., Chen F; School of Chemistry and Chemical Engineering, Yangzhou University, Siwangting Road 180, 225002, Yangzhou, P. R. China.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Sep 11; Vol. 30 (51), pp. e202400963. Date of Electronic Publication: 2024 Aug 21.
DOI: 10.1002/chem.202400963
Abstrakt: The development of innovative methods for synthesizing silylcyclopentene compounds is particularly important for enriching and improving the synthetical toolbox of organosilicon compounds. Herein, a facile approach has been developed for the synthesis of silylcyclopentenes promoted by mechanochemically generated organolithium species as silicon nucleophiles under ball milling conditions, avoiding the requirement of large amounts of bulk solvent. This operationally simple method demonstrates good functional group compatibility, which provides a great opportunity for further exploration of the synthetic applications of silylcyclopentenes. Density functional theory calculations indicated that the transient lithiosilole intermediates undergo a stepwise nucleophilic addition process, which governs this mechanic-force-promoted [4+1] cycloaddition reaction.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
Externí odkaz: