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Redox-triggered C-C coupling of diols and alkynes: synthesis of ?,?-unsaturated ?-hydroxyketones and furans by ruthenium-catalyzed hydrohydroxyalkylation.

ABSTRACT: Direct ruthenium-catalyzed CC coupling of alkynes and vicinal diols to form ?,?-unsaturated ketones occurs with complete levels of regioselectivity and good to complete control over the alkene geometry. Exposure of the reaction products to substoichiometric quantities of p-toluenesulfonic acid induces cyclodehydration to form tetrasubstituted furans. These alkyne-diol hydrohydroxyalkylations contribute to a growing body of merged redox-construction events that bypass the use of premetalated reagents and, hence, stoichiometric quantities of metallic by-products.

SUBMITTER: McInturff EL

PROVIDER: S-EPMC4037928 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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Redox-triggered C-C coupling of diols and alkynes: synthesis of β,γ-unsaturated α-hydroxyketones and furans by ruthenium-catalyzed hydrohydroxyalkylation.

McInturff Emma L EL Nguyen Khoa D KD Krische Michael J MJ

Angewandte Chemie (International ed. in English) 20140301 12

Direct ruthenium-catalyzed CC coupling of alkynes and vicinal diols to form β,γ-unsaturated ketones occurs with complete levels of regioselectivity and good to complete control over the alkene geometry. Exposure of the reaction products to substoichiometric quantities of p-toluenesulfonic acid induces cyclodehydration to form tetrasubstituted furans. These alkyne-diol hydrohydroxyalkylations contribute to a growing body of merged redox-construction events that bypass the use of premetalated reag ...[more]

PMID: 24677357

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