American Chemical Society
jo3c01149_si_001.pdf (8.09 MB)

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

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journal contribution
posted on 2023-07-29, 13:05 authored by Sandip Bag, Shubham Ojha, Sreelakshmi Venugopalan, Basudev Sahoo
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.