Domino Conjugate Addition-1,4-Aryl Migration for the Synthesis of α,β-Difunctionalized Amides.

Autor: Zhang H; Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria.; Vienna Doctoral School in Chemistry, University of Vienna, Währinger Straße 42, 1090 Vienna, Austria.; Christian-Doppler Laboratory for Entropy-Oriented Drug Design, Josef-Holaubek-Platz 2, 1090 Vienna, Austria., Xiao Y; Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria.; Vienna Doctoral School in Chemistry, University of Vienna, Währinger Straße 42, 1090 Vienna, Austria.; CeMM Research Center for Molecular Medicine of the Austrian Academy of Sciences, Lazarettgasse 14, AKH BT 25.3, 1090 Vienna, Austria., Lemmerer M; Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria.; Vienna Doctoral School in Chemistry, University of Vienna, Währinger Straße 42, 1090 Vienna, Austria., Bortolato T; Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria., Maulide N; Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria.; Christian-Doppler Laboratory for Entropy-Oriented Drug Design, Josef-Holaubek-Platz 2, 1090 Vienna, Austria.; CeMM Research Center for Molecular Medicine of the Austrian Academy of Sciences, Lazarettgasse 14, AKH BT 25.3, 1090 Vienna, Austria.
Jazyk: angličtina
Zdroj: JACS Au [JACS Au] 2024 Jun 17; Vol. 4 (7), pp. 2456-2461. Date of Electronic Publication: 2024 Jun 17 (Print Publication: 2024).
DOI: 10.1021/jacsau.4c00378
Abstrakt: 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 SO 2 . 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 S N Ar 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.
Competing Interests: The authors declare no competing financial interest.
(© 2024 The Authors. Published by American Chemical Society.)
Databáze: MEDLINE
Externí odkaz: