Ruthenium-catalyzed self-coupling of primary and secondary alcohols with the liberation of dihydrogen.
J Org Chem
; 78(13): 6593-8, 2013 Jul 05.
Article
em En
| MEDLINE
| ID: mdl-23725014
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.
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Base de dados:
MEDLINE
Assunto principal:
Compostos Organometálicos
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Rutênio
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Álcoois
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Hidrogênio
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Cetonas
Idioma:
En
Ano de publicação:
2013
Tipo de documento:
Article