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Paper | Regular issue | Vol 63, No. 8, 2004, pp.1839-1847
Published online, 18th June, 2004
DOI: 10.3987/COM-04-10116
SnCl4-Promoted Ethenylation Reaction of Hydroxylated Heteroarenes

Kensuke Akamatsu, Ryo Amemiya, and Masahiko Yamaguchi*

*Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Sendai 980-8578, Japan


Reaction of hydroxylated heteroarenes and acetylene in the presence of SnCl4 and Bu3N (or Et3N) gives the corresponding ethenylated arenes. The reaction takes place at the neighboring position of the hydroxy group, and is applicable to quinolines, an isoquinoline, pyridines, and N-trifluoromethanesulfonylated indoles provided that the optimized conditions for the ethenylation and workup are employed.