ArticleJournal of the American Chemical Society2026
Highly Catalytic Allylation of Native Carbohydrates in Water with Indium: Kinetic, Mechanistic, and Spectroscopic Studies.
Article in Journal of the American Chemical Society, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Nucleophilic allylation reactions mediated by indium have served admirably, particularly in the Barbier-type allylation of unprotected carbohydrates in protic media. Allylations of aldehydes, ketones, and hydrazones that are catalytic in indium have been described with In(III), In(I), and indium metal and have been extended to native carbohydrates in our recently reported indium metal-catalyzed allylation using allylboronic acid pinacol ester (allylBpin). Whereas the mechanism of the Barbier-type allylation has been thoroughly investigated (albeit not with carbohydrate substrates), mechanistic studies of the catalytic reactions are scarce. In this report, we disclose detailed mechanistic investigations of the indium metal-catalyzed allylation of sugars in water/methanol mixtures, which reveal four critical aspects: (1) the true catalyst is a soluble In(III) species generated in trace quantities from the oxide/hydroxide layer on the indium metal surface under the reaction conditions, (2) the S-shaped kinetic profile observed with indium metal is explained by autoinduction as the combination of boric acid and the allylated product (1-allylsorbitol) lowers the reaction pH thereby increasing the concentration of soluble indium(III), (3) the active nucleophiles are monoallylindium(III) or diallylindium(III) intermediates (as characterized by
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