Deprotective Functionalization: A Direct Conversion of Nms‐Amides to Carboxamides Using Carboxylic Acids

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.

Objekt anzeigen

• Standort: Deutsche Nationalbibliothek Frankfurt am Main
• Umfang: Online-Ressource
• Sprache: Englisch

Verweise und Beziehungen

• Erschienen in: Deprotective Functionalization: A Direct Conversion of Nms‐Amides to Carboxamides Using Carboxylic Acids ; day:19 ; month:03 ; year:2024 ; extent:8 ; Angewandte Chemie / International edition. International edition ; (19.03.2024) (gesamt 8)

Beteiligte, Orts- und Zeitangaben

• Urheber: Spieß, Philipp ; Brześkiewicz, Jakub ; Meyrelles, Ricardo ; Just, David ; Maulide, Nuno

Weitere Informationen

• DOI: 10.1002/anie.202318304
• URN: urn:nbn:de:101:1-2024032013324209424855
• Rechteinformation: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.