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26.1.7.1.6 Variation 6: By Ruthenium-Catalyzed Hydration

DOI: 10.1055/sos-SD-026-00312

Figadère, B.; Franck, X.Science of Synthesis, (200526404.

Ruthenium(III) salts catalyze the hydration of alkynes. Internal symmetrical alkynes give the expected ketones, whereas terminal alkynes, depending on the reaction conditions, give either the Markovnikov or the anti-Markovnikov products. Thus, terminal alkynes when refluxed in formic acid in the presence of dodecacarbonyltriruthenium(0), in the absence of water, give methyl ketones 7 (R2=H) in good yields (Scheme 8).[‌1‌] Several authors have reported the anti-Markovnikov ruthenium(II)-catalyzed addition of water to terminal alkynes, giving aldehydes as major products.[‌24‌‌26‌]

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