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Highly Recyclable Fluoride for Enhanced Cascade Hydrosilylation–Cyclization of Levulinates to γ-Valerolactone at Low Temperatures

Author:
Zhao, Wenfeng, Yang, Tingting, Li, Hu, Wu, Weibo, Wang, Zhongwei, Fang, Chengjiang, Saravanamurugan, Shunmugavel, Yang, Song
Source:
ACS sustainable chemistry 2017 v.5 no.11 pp. 9640-9644
ISSN:
2168-0485
Subject:
Lewis bases, activation energy, ambient temperature, catalysts, fluorides, leaching, liquids
Abstract:
A facile and benign catalytic route has been developed to quantitatively yield γ-valerolactone (GVL; ca. 97%) from biomass-based levulinates at room temperature to 80 °C by using easily available polymethylhydrosiloxane (PMHS) and KF as the liquid H-donor and recyclable catalyst, respectively. No extra step was required to liberate GVL from the in situ-formed siloxane, and this catalytic system exhibited a lower activation energy (40.9 kJ/mol) compared to previously reported ones. The deuterium-labeled study further demonstrated the reaction proceeding through cascade hydrosilylation and cyclization with fluoride successively acting as the nucleophile and base. In addition, the PMHS-derived resin was extremely favorable to restrain the leaching of fluoride and maintain its constant activity for at least six cycles.
Agid:
5852537