One-pot synthesis of N-methylindoles from N-methylanilines and of benzofurans from phenols using transition-metal carbene X-H insertion reactions |
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Authors: | Mark A Honey Ian B Campbell Christopher J Moody |
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Institution: | a School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK b GlaxoSmithKline, Gunnels Wood Road, Stevenage SG1 2NY, UK |
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Abstract: | Transition-metal carbene X-H insertion reactions (X=N or O) have been employed in the simple conversion of anilines and phenols into indoles and benzofurans, respectively. Thus copper(II) catalyzed N-H insertion reactions of α-diazo-β-ketoesters with N-methylanilines followed by treatment with acidic ion-exchange resin gives indoles. In a similar manner, dirhodium(II) catalyzed O-H insertion reactions of α-diazo-β-ketoesters with phenols followed by treatment with PPA gives benzofurans. |
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