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TiCl4-Catalyzed Indirect Anti-Markovnikov Hydration of Alkynes: Application to the Synthesis of Benzo[b]furans

Lutz Ackermann* and Ludwig T. Kaspar

*Institut für Organische und Biomolekulare Chemie, Georg-August-Universitaet Goettingen, Tammannstr. 2, D-37077 Goettingen, Germany, Email: Lutz.Ackermannchemie.uni-goettingen.de

L. Ackermann, L. T. Kaspar, J. Org. Chem., 2007, 72, 6149-6153.

DOI: 10.1021/jo070887i (free Supporting Information)


Abstract

An efficient, indirect anti-Markovnikov hydration of unsymmetrically substituted terminal and internal alkynes is based on TiCl4-catalyzed hydroamination reactions. Its application to ortho-alkynylhaloarenes, followed by a copper-catalyzed O-arylation, provides substituted benzo[b]furans.

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Key Words

hydration of alkynes, benzo[b]furans


ID: J42-Y2007-2530