An umpolung strategy for intermolecular [2 + 2 + 1] cycloaddition of aryl aldehydes and nitriles: a facile access to 2,4,5-trisubstituted oxazoles?

Chemical Science Pub Date: 2022-06-11 DOI: 10.1039/D2SC00046F

Abstract

We have described the first example of an umpolung strategy for intermolecular [2 + 2 + 1] cycloaddition between two aryl aldehydes and a nitrile under the influence of TMSOTf that proceeds through the formation of N–C, O–C and C–C bonds providing a simple synthetic protocol for obtaining 2,4,5-trisubstituted oxazoles.

Graphical abstract: An umpolung strategy for intermolecular [2 + 2 + 1] cycloaddition of aryl aldehydes and nitriles: a facile access to 2,4,5-trisubstituted oxazoles
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