Bag Sandip, Ojha Shubham, Venugopalan Sreelakshmi, Sahoo Basudev
School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram, Thiruvananthapuram - 695551, Kerala, India.
J Org Chem. 2023 Aug 18;88(16):12121-12130. doi: 10.1021/acs.joc.3c01149. Epub 2023 Jul 29.
We describe a visible-light photoredox-catalyzed alkylation/arylative cyclization of -acrylamides─from 2-arylindoles, 2-arylbenzimidazoles, or -substituted anilines─with ketone-derived dihydroquinazolinones, accessing indolo- and benzimidazolo[2,1-]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.
我们描述了一种可见光光氧化还原催化的α-丙烯酰胺的烷基化/芳基化环化反应，该反应以2-芳基吲哚、2-芳基苯并咪唑或N-取代苯胺与酮衍生的二氢喹唑啉酮为原料，生成吲哚并和苯并咪唑并[2,1-a]异喹啉或2-氧代吲哚。通过酮α-C-C键和芳烃C-H键的形式断裂，在C=C键上连续引入烷基和芳基碳源基序，导致形成具有全碳季立体中心的五元环和六元环。这种双碳官能化阐述了未活化脂肪族酮的芳构化驱动的自由基C-C官能化，以构建具有官能团耐受性的多样环状结构。
