Titel
Domino Conjugate Addition-1,4-Aryl Migration for the Synthesis of α,β-Difunctionalized Amides
Autor*in
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Abstract
A domino difunctionalization of sulfonyl(acryl)imides to form β-substituted α-aryl amides is reported. This transformation involves a 1,4-addition followed by a polar Truce–Smiles rearrangement process, entropically driven by release of SO2. A wide range of carbon- and heteroatom-based nucleophiles and sulfonyl imides were employed, allowing rapid access to highly functionalized amides. In contrast to related reactions with a radical pathway, unbiased substrates could be employed. Despite the usual requirement of an electron-poor migrating moiety for the SNAr event, we herein report unique and unprecedented vinylogous migrations of electron-neutral arenes. Additionally, a one-pot process toward β-amido amides starting from acrylic acids has been developed.
Stichwort
AmidesConjugate acid-base pairsGeneticsRearrangementSubstitution reactions
Objekt-Typ
Sprache
Englisch [eng]
Persistent identifier
phaidra.univie.ac.at/o:2080662
Erschienen in
Titel
JACS Au
Band
4
Ausgabe
7
ISSN
2691-3704
Erscheinungsdatum
2024
Seitenanfang
2456
Seitenende
2461
Publication
American Chemical Society (ACS)
Fördergeber
Europäische Union (alle Programme) — CoG682002
Erscheinungsdatum
2024
Zugänglichkeit
Rechte
Rechteangabe
© 2024 The Authors
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