Decatungstate‐Photocatalyzed Dearomative Hydroacylation of Indoles: Direct Synthesis of 2‐Acylindolines. Issue 56 (17th August 2022)

• Record Type: Journal Article
• Authors: Varlet, Thomas; Bouchet, Damien; Van Elslande, Elsa; Masson, Géraldine
• Is Part Of: Chemistry. Volume 28:Issue 56(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-08-17
• Subjects: dearomatization -- decatungstate -- hydroacylation -- indole -- photocatalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202201707
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: We report herein a convenient and scalable dearomative hydroacylation reaction of indoles. Employing readily available aldehydes as the acyl source and TBADT as an inexpensive direct HAT photocatalyst, a variety of indoles derivatives were converted into synthetically interesting 2‐acylindolines in good to excellent yields as well as great diastereoselectivity under mild conditions. An asymmetric version of the reaction was successfully developed and an experimental mechanistic investigation was carried out in order to gain further insights on the assumed reaction pathway. Abstract : "A POM out of the blue" . Decatungstate anion photocatalyzed a mild dearomatization of indoles to access 2‐acylindolines via direct hydrogen atom transfer under purple‐light irradiation.