Photocatalyzed E→Z Contra-thermodynamic Isomerization of Vinyl Boronates with Binaphthol |
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Authors: | Thibaud Brégent Prof Dr Jean-Philippe Bouillon Prof Dr Thomas Poisson |
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Institution: | Normandie Université, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France |
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Abstract: | The photocatalytic contra-thermodynamic E→Z isomerization of vinyl boronates by using a binaphthol catalyst is disclosed. The reaction, based on the transient formation of a suitable chromophore with a BINOL derivative as the catalyst, allowed geometrical isomerization in good-to-excellent Z/E ratio and excellent-to-quantitative yields. The mechanism of this E→Z contra-thermodynamic isomerization was studied, and the formation of a transient chromophore species is suggested. |
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Keywords: | alkenes binaphthol boron isomerization photochemistry |
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