Photocatalytic Alkylation/Arylative Cyclization of N‑Acrylamides of N‑Heteroarenes and Arylamines with Dihydroquinazolinones from Unactivated Ketones

• Published in: Journal of organic chemistry Vol. 88; no. 16; pp. 12121 - 12130
• Main Authors: Bag, Sandip, Ojha, Shubham, Venugopalan, Sreelakshmi, Sahoo, Basudev
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 18.08.2023; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; PHOTOCHEMISTRY; ALKYLARYLATION; RADICALS
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/acs.joc.3c01149

We describe a visible-light photoredox-catalyzed alkylation/arylative cyclization of N-acrylamidesfrom 2-arylindoles, 2-arylbenzimidazoles, or N-substituted anilineswith ketone-derived dihydroquinazolinones, accessing indolo- and benzimidazolo­[2,1-a]­isoquinolines or 2-oxindoles. The consecutive incorporation of alkyl- and aryl-carbogenic motifs across a C=C bond via formal cleavage of ketone α-C–C and arene C–H bonds leads to the formation of five- and six-membered rings, with an all-carbon quaternary stereocenter. This dicarbofunctionalization elaborates aromatization-driven radical C–C functionalization of unactivated aliphatic ketones to construct diverse cyclic structures with functionality tolerance.