Synfacts 2006(9): 0880-0880  
DOI: 10.1055/s-2006-942068
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Ru-Catalyzed Propargylation of Aromatics and Heteroaromatics

Contributor(s): Victor Snieckus, Yigang Zhao
Y. Inada, M. Yoshikawa, M. D. Milton, Y. Nishibayashi*, S. Uemura
Kyoto University and The University of Tokyo, Japan
Further Information

Publication History

Publication Date:
23 August 2006 (online)

Significance

Inter- and intramolecular Ru-catalyzed propargylation of aromatic and heteroaromatic compounds is reported. The reaction proceeds using catalyst 1 in the presence of ammonium tetrafluoroborate under mild conditions leading to regioselective formation of propargylated furans, indoles, as well as aromatics in moderate to high yields. An interesting intramolecular version of this reaction, shown in the scheme, was also established. Some limitations for the propargylation process have been noted, e.g.,acetanilide, 1,3-dimeth­oxybenzene, p-xylene and toluene, among others, failed.