Titel
Deprotective Functionalization: A Direct Conversion of Nms‐Amides to Carboxamides Using Carboxylic Acids
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Abstract
The nature of protecting group chemistry necessitates a deprotection step to restore the initially blocked functionality prior to further transformation. As this aspect of protecting group manipulation inevitably adds to the step count of any synthetic sequence, the development of methods enabling simultaneous deprotection and functionalization (“deprotective functionalization”—distinct from “deprotection followed by functionalization”) is appealing, as it has the potential to improve efficiency and streamline synthetic routes. Herein, we report a deprotective functionalization of the newly introduced Nms-amides guided by density functional theory (DFT) analysis, which exploits the inherent Nms reactivity. Mechanistic studies further substantiate and help rationalize the exquisite reactivity of Nms-amides, as other commonly used protecting groups are shown not to exhibit the same reactivity patterns. The practicality of this approach was ultimately demonstrated in selected case studies.
Stichwort
DeprotectionProtecting GroupSulfonamidesAmidesCarboxylic Acids
Objekt-Typ
Sprache
Englisch [eng]
Persistent identifier
phaidra.univie.ac.at/o:2067802
Erschienen in
Titel
Angewandte Chemie International Edition
Band
63
Ausgabe
19
ISSN
1433-7851
Erscheinungsdatum
2024
Publication
Wiley
Fördergeber
Europäische Union (alle Programme) — 682002
Erscheinungsdatum
2024
Zugänglichkeit
Rechte
Rechteangabe
© 2024 The Authors
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