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Metal-Free Catalytic Nucleophilic Substitution of Propargylic Alcohols

Roberto Sanz*, Alberto Martínez, Julia M. Álvarez-Gutiérrez, Félix Rodríguez

*Área de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Missael Bañuelos s/n, 09001 Burgos, Spain, Email:

R. Sanz, A. Martinez, J. M. Alvarez-Gutierrez, F. Rodriquez, Eur. J. Org. Chem., 2006, 1383-1386.

DOI: 10.1002/ejoc.200500960 (free Supporting Information)


p-Toluenesulfonic acid efficiently catalyzes direct nucleophilic substitutions of the hydroxy groups of propargylic alcohols with a large variety of carbon- and heteroatom-centered nucleophiles. Reactions can be conducted under mild conditions and in air without the need for dried solvents.

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Key Words

Aromatic substitution, Propargylation, Homogeneous catalysis, Propargylic alcohols, Nucleophilic substitution, Ethers, Sulfides, Amines, Synthetic methods

ID: J24-Y2006-790