Tetrahedron

One-pot synthesis of N-methylindoles from N-methylanilines and of benzofurans from phenols using transition-metal carbene X–H insertion reactions

MA Honey, AJ Blake, IB Campbell, BD Judkins…

Index: Honey, Mark A.; Blake, Alexander J.; Campbell, Ian B.; Judkins, Brian D.; Moody, Christopher J. Tetrahedron, 2009 , vol. 65, # 44 p. 8995 - 9001

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Citation Number: 21

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 ...