Di-tert-butylsilylene as a protecting group for substituted salicylic acids
2020
Pongdee, Gabriel J. | Bell, Kathryn G. | Prestwood, Peri R. | Pongdee, Rongson
The use of di-tert-butylsilyl bis(trifluoromethanesulfonate) has been used to form cyclic protecting groups for substituted salicylic acids. The reaction works well in the presence of a variety of electron-donating groups (EDG) affording the protected compounds in moderate to excellent yields (70–99%) in most cases. In addition, a handful of electron-withdrawing groups (EWG) also provided the corresponding protected silylene derivatives in good yields (77–83%). However, substrates bearing additional ortho -substitution of the carboxylic acid moiety as well as strongly deactivating groups on the aromatic ring did not undergo reaction.
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