Breslow intermediates are very often elusive species whose application in frustrated Lewis pair (FLP) chemistry is unprecedented. Described herein is the use of a masked form of an O-borylated Breslow (OBB) intermediate that performs FLP-type activation of the carbonyl function of five different benzaldehyde derivatives with complete diastereoselectivity. The resulting compounds are characterised in solution by NMR spectroscopy (compounds 4-8) and in solid state by Xray diffraction analysis (compounds 4-6). A combined kinetic and theoretical investigation reveals the associative nature of the rate determining step and suggests that the OBB intermediate part is never released during the whole process.
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