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Abstract
Solid-phase conversion of aromatic acetylenes 1 to the corresponding carboxylic acids 2, α-ketocarboxylic acids 3, and methyl ketones 4 is described. Resin-bound TMS-acetylenes 1 were prepared from PEGA resin by Fmoc-based peptide synthesis. The desilylation of 1 with TBAF (4 equiv) followed by OsO4/NMO/HMTA-mediated oxidative cleavage to give the carboxylic acids 2. α-Ketocarboxylic acids 3 were obtained by direct treatment of 1 with OsO4/NMO/HMTA and ketones 4 by acid-mediated hydration of 1 using aqueous TFA.
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