Herein, we report a visible-light mediated organophotoredox-catalyzed Csp2-H alkylation of N-heteroarenes with dihydroquinazolines, from aliphatic ketones, under oxidative condition. This protocol represents a metal free approach to effectively construct C-C bond via Minisci-type reaction, formally activating native C-H bond of N-heteroarene and -C-C bond of readily available ketones. The mild nature of this method accommodates a large variety of N-heteroarenes as well as ketones, tolerating distinct functional groups.
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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