3 years ago

Isocyanurate Formation During Oxazolidinone Synthesis from Epoxides and Isocyanates Catalysed by a Chromium(Salphen) Complex

Isocyanurate Formation During Oxazolidinone Synthesis from Epoxides and Isocyanates Catalysed by a Chromium(Salphen) Complex
Xiao Wu, Jess Mason, Michael North
Chromium(salphen) complex 10 is found to be a catalyst for the preparation of oxazolidinones from epoxides and isocyanates. Using the optimal reaction conditions (1.5 mol % of chromium(salphen) complex 10 at 80 °C in toluene for 4 hours), six epoxides were reacted with five isocyanates, providing 15 oxazolidinones in up to 90 % yield. With electron-deficient isocyanates, cyclotrimerisation of the isocyanate to the corresponding isocyanurates is a competing reaction, showing the importance of matching catalyst activity to that of the substrates. A tale of two reactions: A chromimium(salphen) complex catalyses the formation of oxazolidinones from epoxides and isocyanates. However, with particularly electron-deficient isocyanates, the complex catalyses cyclotrimerisation of the isocyanate to an isocyanurate instead (see scheme).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702948

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