Advertisement

Reactions of lithiated aromatic heterocycles with carbon monoxide

Authors

  • Guadalupe E. García Liñares,

    1. Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pab. II, P. 3, Ciudad Universitaria, 1428 Buenos Aires, Argentina
    Search for more papers by this author
  • Norma S. Nudelman

    Corresponding author
    1. Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pab. II, P. 3, Ciudad Universitaria, 1428 Buenos Aires, Argentina
    • Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pab. II, P. 3, Ciudad Universitaria, 1428 Buenos Aires, Argentina
    Search for more papers by this author

Abstract

The reaction of lithium derivatives of aromatic heterocycles with carbon monoxide was studied under several reaction conditions: 2-furyllithium afforded only one product, the tetrahydro-2-furaldehyde (25% yield). On the other hand, 2-thienyllithium and 5-methyl-2-furyllithium gave two and five products, respectively. Although in relatively low yields, formation of highly functionalized compounds takes place in a fast process under mild conditions. For 1,4-dihydroxy-1,4-bis(5-methyl-2-furanyl)butane-2,3-dione, reaction conditions were achieved to obtain this difficult to prepare derivative in 50% yield. To the best of our knowledge, this is the first report on the reaction of lithiated aromatic heterocycles with CO: evidence is given on the involvement of proton transfers in the reactions of 2-furyllithium and 2-thienyllithium, while the reaction of 5-methyl-2-furyllithium seems to proceed through an electron transfer as the first step. Copyright © 2003 John Wiley & Sons, Ltd.

Ancillary