Visible-Light-Photocatalyzed Dicarbofunctionalization of Conjugated Alkenes with Ketone-Based Dihydroquinazolinones.
Org Lett
; 25(9): 1441-1446, 2023 Mar 10.
Article
em En
| MEDLINE
| ID: mdl-36820645
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.
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MEDLINE
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En
Ano de publicação:
2023
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Article