Ruthenium-catalyzed self-coupling of primary and secondary alcohols with the liberation of dihydrogen

Ilya Makarov, Robert Madsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

The dehydrogenative self-condensation of primary and secondary alcohols has been studied in the presence of RuCl2(IiPr)(p-cymene). The conversion of primary alcohols into esters has been further optimized by using magnesium nitride as an additive, which allows the reaction to take place at a temperature and catalyst loading lower than those described previously. Secondary alcohols were dimerized into racemic ketones by a dehydrogenative Guerbet reaction with potassium hydroxide as the additive. The transformation gave good yields of the ketone dimers with a range of alkan-2-ols, whereas more substituted secondary alcohols were unreactive. The reaction proceeds by dehydrogenation to the ketone, followed by an aldol reaction and hydrogenation of the resulting enone. © 2013 American Chemical Society.
Original languageEnglish
JournalJournal of Organic Chemistry
Volume78
Issue number13
Pages (from-to)6593-6598
ISSN0022-3263
DOIs
Publication statusPublished - 2013

Keywords

  • Condensation reactions
  • Ketones
  • Loading

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