Di-tert-butylsilylene as a protecting group for substituted salicylic acids

[Display omitted] •Di-tert-butylsilylene serves as an effective protecting group for substituted salicylic acids.•Electron-rich salicylic acids are protected in good to excellent yields (70–99%).•Electron-poor salicylic acids are protected in good yields (77–83%).•Deprotection occurs readily upon tr...

Full description

Saved in:

Bibliographic Details
Published in:	Tetrahedron letters Vol. 61; no. 48; p. 152465
Main Authors:	Pongdee, Gabriel J., Bell, Kathryn G., Prestwood, Peri R., Pongdee, Rongson
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 26-11-2020
Subjects:	Protecting groups Reaction development Salicylic acids Silylenes Salicylic acids Silylenes Protecting groups Reaction development
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

Description
Summary:	[Display omitted] •Di-tert-butylsilylene serves as an effective protecting group for substituted salicylic acids.•Electron-rich salicylic acids are protected in good to excellent yields (70–99%).•Electron-poor salicylic acids are protected in good yields (77–83%).•Deprotection occurs readily upon treatment with tetrabutylammonium fluoride. 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.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2020.152465