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- Title
Redox-Triggered CC Coupling of Diols and Alkynes: Synthesis of β,γ-Unsaturated α-Hydroxyketones and Furans by Ruthenium-Catalyzed Hydrohydroxyalkylation.
- Authors
McInturff, Emma L.; Nguyen, Khoa D.; Krische, Michael J.
- Abstract
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 reagents and, hence, stoichiometric quantities of metallic by-products.
- Subjects
OXIDATION-reduction reaction; GLYCOL synthesis; ALKYNE synthesis; RUTHENIUM catalysts; KETONE synthesis; STOICHIOMETRIC combustion
- Publication
Angewandte Chemie International Edition, 2014, Vol 53, Issue 12, p3232
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201311130