Heterocycles p. 669 - 684 (2003)
Update date:2022-08-03
Topics: Addition Scope Limitations Photodecarboxylative Carboxylates Phthalimides
Oelgemoeller, Michael
Cygon, Peter
Lex, Johann
Griesbeck, Axel G.
Intermolecular photoinduced decarboxylative additions of a series of alkylcarboxylates to N-substituted phthalimides gave the corresponding hydroxyphthalimidines in moderate to high yields of 39-89%. The potassium salt of 1-adamantanecarboxylic acid predominately underwent simple decarboxylation when irradiated in the presence of N-methylphthalimide. In case of phthalimides carrying suitable leaving groups within the N-side chain, decarboxylation, retro-Aldol cleavage or decarbonylation preceded the intermolecular addition step.
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