Download PDF
Synfacts 2007(8): 0864-0864  
DOI: 10.1055/s-2007-968735
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Conjugated Enynes and Substituted Indoles from 1-Alkynes

Contributor(s): Paul Knochel, Andrei Gavryushin
F. Liu, D. Ma*
Shanghai Institute of Organic Chemistry, P. R. of China
Further Information

Publication History

Publication Date:
24 July 2007 (online)

    Permissions and Reprints

Significance

Terminal alkynes can be coupled with alkenyl iodides under copper(I) catalysis, affording the corresponding enynes in good to excellent yields with retention of the double-bond configuration. Many of these products are of interest for pharmacology and materials science. Substituted o-bromotrifluoroacetanilides react with 1-alkynes to 2-substituted indoles. This type of Sonogashira coupling does not use expensive Pd catalysts and is therefore more convenient for large-scale industrial applications than most of the existing protocols.