Abstract
Amide transformations involving C-N bond cleavage are recognized as difficult reactions owing to the inert nature of amides resulting from resonance. Accordingly, a strong inductive effect and geometrical distortion reasonably decrease the resonance stabilization to attenuate the C-N linkage. Although the conversion of such activated amides has been studied intensively, reaction systems for unactivated amides are underdeveloped. We herein report that a zinc(II) trifluoromethanesulfonate [Zn(OTf)(2)] catalyst achieves the esterification of a wide range of unactivated tertiary amides with the assistance of intramolecular acyl rearrangement. The reaction was applied to the one-pot removal of various amide-based directing groups under mild reaction conditions to afford the corresponding esters in high yields.
Dokumententyp: | Zeitschriftenartikel |
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Fakultät: | Chemie und Pharmazie > Department Chemie |
Themengebiete: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
ISSN: | 1434-193X |
Sprache: | Englisch |
Dokumenten ID: | 54302 |
Datum der Veröffentlichung auf Open Access LMU: | 14. Jun. 2018, 09:55 |
Letzte Änderungen: | 04. Nov. 2020, 13:33 |