Unexpected one-step synthesis of 3-benzoyl-2-phenylbenzofurans under Wittig conditions

作者：Begala Michela^*; Caboni Pierluigi; Joao Matos Maria; Delogu Giovanna Lucia

来源：Tetrahedron Letters, 2018, 59(18): 1711-1714.

DOI：10.1016/j.tetlet.2018.03.048

• Wittig reaction
• 2-Phenylbenzofurans
• 3-Aroylbenzofurans

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.

• 出版日期2018-5-2