Pd/Cu‐Catalyzed Cross‐Coupling of Densely Substituted Propargylamines with Aromatic Acyl Chlorides Followed by the Treatment with a Base: Access to Dihydro‐3H‐Pyrrol‐3‐Ones

• Published in: Advanced synthesis & catalysis Vol. 365; no. 1; pp. 53 - 67
• Main Authors: Volkov, Pavel A., Khrapova, Kseniya O., Telezhkin, Anton A., Bidusenko, Ivan A., Schmidt, Elena Yu, Albanov, Alexander I., Trofimov, Boris A.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 10.01.2023; Wiley Subscription Services, Inc
• Subjects: acyl chlorides; aminoacetylenic ketones; Chemistry; Chemistry, Applied; Chemistry, Organic; Chlorides; Cross coupling; cyclization; Ethanol; Ketones; Physical Sciences; propargylamines; pyrrol-3-ones; Science & Technology; pyrrol-3-ones; propargylamines; ALCOHOLS; acyl chlorides; aminoacetylenic ketones; ACID; PYRROLIN-4-ONES; CHEMISTRY; cyclization
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.202201179

Pd/Cu‐catalyzed cross‐coupling of propargylamines with aromatic acyl chlorides (PdCl2, CuI, Ph3P, 40–45 °C) provides α‐aryl(hetaryl)aminoacetylenic ketones in a yield of up to 97%. The latter undergo cyclization to 1,2,5‐triaryl(hetaryl)‐1,2‐dihydro‐3H‐pyrrol‐3‐ones in up to 93% yield after the treatment with KOH or Et2NH (40–55 °C, aqueous ethanol). The one‐pot synthesis of the pyrrol‐3‐ones (in up to 62% yields) by consecutive treatment of the above propargylamines with acyl chlorides (PdCl2/CuI/Ph3P) and a base (KOH) in aqueous ethanol has been also developed.