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- W3203084328 abstract "A C-H bond cleavage-enabled aerobic ring-opening reaction of 2-aminobenzofuran-3(2H)-ones formed in situ by hemiacetals with a variety of amines is reported. This simple one-pot reaction provides an alternative approach to obtain o-hydroxyaryl glyoxylamides in excellent yields of up to 97%. Alkylamines react with hemiacetals via a catalyst-free dehydration condensation to generate 2-aminobenzofuran-3(2H)-ones. The in situ formed semicyclic N,O-acetals undergo the same amine-initiated C-H bond hydroxylation in air under mild conditions to afford ring-opening products. Similarly, arylamines were investigated as substrates for a two-step tandem process involving a DPP-catalyzed condensation followed by a Et2NH-mediated C-H hydroxylation. Unlike the previously reported functionalization of N,O-acetals via a C-O or C-N cleavage, the aerobic oxidative C-H hydroxylation in this reaction, which is promoted by using stoichiometric amounts of alkylamines as both a Lewis base and a reductant at room temperature under atmospheric air, proceeds via α-carbonyl-stabilized carbanion intermediates from the C-H cleavage of N,O-acetals." @default.
- W3203084328 created "2021-10-11" @default.
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- W3203084328 date "2021-01-01" @default.
- W3203084328 modified "2023-09-26" @default.
- W3203084328 title "C-H Bond Cleavage-Enabled Aerobic Ring-Opening Reaction of in Situ Formed 2-Aminobenzofuran-3(2H)-ones" @default.
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- W3203084328 doi "https://doi.org/10.1039/d1ob01755a" @default.
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