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Tetraarylphosphonium Salt-Catalyzed Carbon Dioxide Fixation at Atmospheric Pressure for the Synthesis of Cyclic Carbonates

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posted on 13.09.2016, 00:00 by Yasunori Toda, Yutaka Komiyama, Ayaka Kikuchi, Hiroyuki Suga
Phosphonium salts exhibit great utility in organic synthesis. However, tetraarylphosphonium salts (TAPS) have found limited use as catalysts. We demonstrate the TAPS-catalyzed carbon dioxide fixation at atmospheric pressure for the coupling reaction with epoxides. Five-membered cyclic carbonates were obtained, including enantio-enriched carbonates. Mechanistic studies revealed the origin of the behavior of TAPS to be the in situ formation of an active species by TAPS addition to epoxides via halohydrin intermediates.