Direct palladium-catalyzed C-3 arylation of free (NH)-indoles with aryl bromides under ligandless conditions |
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Authors: | Bellina Fabio Benelli Francesca Rossi Renzo |
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Institution: | Dipartimento di Chimica e Chimica Industriale, University of Pisa, Via Risorgimento 35, 56125 Pisa, Italy. |
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Abstract: | A new method for the efficient, practical, and highly regioselective direct palladium-catalyzed C-3 arylation of free (NH)-indole and its electron-rich 1-unsubstituted derivatives under ligandless conditions is described. The reactions, which are run outside a glovebox without purification of solvent and reagents, involve treatment of free (NH)-indoles with activated, unactivated, and deactivated aryl bromides in refluxing toluene in the presence of K2CO3 as the base and a catalyst system consisting of a combination of Pd(OAc)2 and benzyl(tributyl)ammonium chloride. The experimental results are consistent with a catalytic cycle based on an electrophilic palladation pathway at the 3-position of 1-indolyl potassium salts. |
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