Organic Chemistry Portal

Abstracts

Search:

Methoxy Groups Increase Reactivity of Bifunctional Tetraarylphosphonium Salt Catalysts for Carbon Dioxide Fixation: A Mechanistic Study

Yasunori Toda*, Yutaka Komiyama, Hiroyoshi Esaki, Kazuaki Fukushima* and Hiroyuki Suga*

*Shinshu University, 4-17-1 Wakasato, Nagano 380-8553; Hyogo College of Medicine, 1-1 Mukogawa-Cho, Nishinomiya, Hyogo 663-8501, Japan, Email: ytodashinshu-u.ac.jp, ka-fukushimahyo-med.ac.jp, sugahioshinshu-u.ac.jp

Y. Toda, Y. Komiyama, H. Esaki, K. Fukushima, H. Suga, J. Org. Chem., 2019, 84, 15578-15589.

DOI: 10.1021/acs.joc.9b02581


see article for more reactions

Abstract

Coupling reactions of epoxides with carbon dioxide that proceed at atmospheric pressure at temperatures of less than 100C are challenging. Tetraarylphosphonium salts (TAPS) catalyze the formation of five-membered cyclic carbonates by chemical fixation using 1 atm of carbon dioxide at 60C. Electron-donating groups enhanced the reactivity of the used TAPS.

see article for more examples


proposed mechanism



A Phosphonium Ylide as a Ligand for [3 + 2] Coupling Reactions of Epoxides with Heterocumulenes under Mild Conditions

Y. Toda, K. Hashimoto, Y. Mori, H. Suga, J. Org. Chem., 2020, 85, 10980-10987.


Key Words

dioxolanones, organocatalysis


ID: J42-Y2019