Gold-catalyzed transformation of 2-alkynyl arylazides: Efficient access to the valuable pseudoindoxyl and indolyl frameworks

Alexander Wetzel (1) , Fabien Gagosz (1)

1 DCSO - Laboratoire de synthèse organique

An element of surprise: A series of functionalized 2-alkynyl arylazides has beed converted into 3-substituted indoles or 2,2-disubstituted indolin-3-ones in the presence of a gold(I) complex. Various oxygen or aryl nucleophiles can be used in this process to trap the intermediate a-imino gold carbene. The structural motifs of the products are found in a large variety of biologically active compounds and natural products. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Domaines: Chimie organique

Alexander Wetzel, Fabien Gagosz. Gold-catalyzed transformation of 2-alkynyl arylazides: Efficient access to the valuable pseudoindoxyl and indolyl frameworks. Angewandte Chemie International Edition, 2011, 50 (32), pp.7354-7358. ⟨10.1002/anie.201102707⟩. ⟨hal-00950028⟩