Visible-Light-Photocatalyzed Dicarbofunctionalization of Conjugated Alkenes with Ketone-Based Dihydroquinazolinones
Pinku Prasad Mondal, Subham Das, Sreelakshmi Venugopalan, Malavika Krishnan, Basudev Sahoo
Abstract
A visible-light-photocatalyzed 1,2-arylalkylation of N -(arylsulfonyl)acrylamides with ketone-based dihydroquinazolinones is described. The formal C–C bond cleavage of aliphatic ketones is unified with tandem radical alkylation/1,4-aryl migration/desulfonylation to forge two different types of vicinal C–C bonds and construct an all-carbon quaternary α-stereocenter, thus enhancing the carbogenic complexity and tolerating diverse functionalities. Additional to telescopic synthesis and product diversification, this method features a radical dicarbofunctionalization of conjugated N -(arylsulfonyl)acrylamides with a nucleophilic alkyl radical precursor (dihydroquinazolinone) utilizing oxygen as a green oxidant at ambient temperature.