The palladium-tributylammonium formate reagent in the stereoselective hydrogenation,and stereo- and regioselective hydroarylation of alkyl 4-hydroxy-2-alkynoates: a route to substituted butenolides |
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| Affiliation: | 1. Dipartimento di Chimica, Ingegneria Chimica e Materiali, Università degli Studi, Via Assergi 4, 67100 L''AquilaItaly;2. Istituto di Chimica Organica, Facoltà di Farmacia, Univeraità degli Studi “La Sapienza”, P.le A. Moro 5, 00185 RomaItaly;3. Dipartimento di Scienze Chimiche, Università degli Studi, Via S. Agostino 1, 62032 CamerinoItaly;1. Syngenta Crop Protection AG, Crop Protection Research, Research Chemistry, Schaffhauserstrasse 101, CH-4332, Switzerland;2. Bogazici University, Department of Chemistry, Bebek, 34342 Istanbul, Turkey;1. Hefei National Laboratory for Physical Sciences at Microscale, University of Science and Technology of China, 230026 Hefei, China;2. Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation |
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| Abstract: | The reaction of aryl iodides with alkyl 4-hydroxy-2-alkynoates in the presence of formic acid, tri-n-butylamine and a palladium(II) catalyst provides a convenient route to functionalized substituted butenolides through a one pot hydroarylation/cyclization reaction. In the presence of formic acid, tri-n-butylamine and a palladium(II) catalyst, alkyl 4-hydroxy-2-alkynoates undergo a one pot hydrogenation/cyclization reaction to the butenolide ring. By increasing the excess of formic acid, direct formation of saturated γ-lactones can be observed. Reactions occur with high stereoselectivity and, in the case of the hydroarylation, with good regioselectivity. |
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