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

Yasunori Toda*, Kousuke Hashimoto, Yoko Mori and Hiroyuki Suga*

*Department of Materials Chemistry, Faculty of Engineering, Shinshu University, 4-17-1 Wakasato, Nagano 380-8553, Japan, Email: ytodashinshu-u.ac.jp, sugahioshinshu-u.ac.jp

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

DOI: 10.1021/acs.joc.0c01101

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Abstract

Complexes of phosphonium ylides and metal halide salts efficiently catalyze the reaction of epoxides with carbon dioxide under mild conditions to provide five-membered cyclic carbonates, including disubstituted cyclic carbonates in good yields. Terminal epoxides could also be converted to N-aryl oxazolidinones with isocyanates using a similar catalytic system.

see article for more examples

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

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

Tetraarylphosphonium Salt-Catalyzed Synthesis of Oxazolidinones from Isocyanates and Epoxides

Y. Toda, S. Gomyou, S. Tanaka, Y. Komiyama, A. Kikuchi, H. Suga, Org. Lett., 2017, 19, 5786-5789.

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Key Words

dioxolanones, oxazolidinones

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ID: J42-Y2020