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DOI: 10.1055/s-0029-1219718
Rhodium-Catalyzed Carbonylative Addition-Cyclization Approach to Furans
J. Dheur, M. Sauthier*, Y. Castanet*, A. Mortreux
Unité de Catalyse et Chimie du Solide, Villeneuve d’Ascq, France
Publication History
Publication Date:
22 April 2010 (online)
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Significance
While attempting the rhodium-catalyzed synthesis of γ-hydroxy ketones by reaction of propargylic alcohols with arylboronic acids, Sauthier, Castanet and co-workers stumbled on an unexpected formation of a furan derivative, formed by dehydrative cyclization of the in situ formed hydroxy enone. An extensive screening involving the solvent, temperature, and rhodium source afforded the optimal conditions as shown in the scheme. The addition of 2.5 mol% LiI led to ˜50% increase in the yield. The role of LiI was not speculated. The yields range from moderate to good, except when the aryl ring contains meta or ortho substituents (<10% yield). The substrate scope was insufficiently studied; most notably heteroaromatic boronic acids were not investigated.