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Photocatalytic E→Z Contra‐Thermodynamic Isomerization of Vinyl Silanes with Lewis Base

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The contra-thermodynamic EZ isomerization of vinyl silanes was reported using rac-BINAP as the photocatalyst. This reaction proceeds via the in situ formation of a chromophoric species, in the presence of catalyst. Under irradiation at 405 nm the interconversion of E-isomers into the Z-congeners were carried out in good to excellent yields and outstanding Z/E selectivities (18 examples) and the reaction mechanism was studied.


Abstract

Herein, we disclosed the contra-thermodynamic EZ isomerization of alkenyl silanes, according to the in situ formation of a chromophoric species, in the presence of rac-BINAP as the catalyst. The reaction carried out in DMSO or CH3CN under irradiation at 405 nm allowed the interconversion of the E-isomers into the Z-congeners in good to excellent yields and outstanding Z/E selectivities, on 18 examples. Finally, the mechanism of this EZ isomerization was studied to get insight into the reaction mechanism.

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