Unexpected one-step synthesis of 3-benzoyl-2-phenylbenzofurans under Wittig conditions |
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Authors: | Michela Begala Pierluigi Caboni Maria João Matos Giovanna Lucia Delogu |
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Affiliation: | 1. Department of Life and Environmental Sciences, University of Cagliari, Via Ospedale 72, 09124 Cagliari, Italy;2. Department of Organic Chemistry, University of Santiago de Compostela, Campus Vida, 15782 Santiago de Compostela, Spain |
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Abstract: | The reaction of 2-hydroxybenzyltriphenylphosphonium bromide with substituted benzoyl chlorides under Wittig conditions, led to 2-phenylbenzofuran derivatives 4a–p and the unexpected formation of 3-benzoyl-2-phenylbenzofuran derivatives 5a–p. Benzoyl chlorides possessing electron-withdrawing groups afforded 3-benzoyl-2-phenylbenzofuran derivatives in higher yields than those with electron-donating groups. This reaction represents a simple and regioselective, one-pot route towards the preparation of deactivated 3-benzoyl-2-phenylbenzofuran compounds which are difficult to obtain by the direct acylation of 2-phenylbenzofurans. |
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Keywords: | Wittig reaction 2-Phenylbenzofurans 3-Aroylbenzofurans |
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