Y. Masuyama, Kana Miyazaki, N. Suzuki
Sep 1, 2013
Citations
0
Influential Citations
4
Citations
Journal
Asian Journal of Organic Chemistry
Abstract
The cyclotrimerization of terminal alkynes, such as ethyl propynoate, arylacetylenes, and alkylacetylenes, catalyzed by a phosphine-free chloro(1,5-cyclooctadiene)iridium(I) dimer ([IrCl(cod)]2) between 40 °C and 100 °C in 1,4-dioxane is induced by a catalytic amount of tin(II) chloride to afford the corresponding 1,2,4-trisubstituted and/or 1,3,5-trisubstituted benzenes. Terminal α,ω-diynes, such as 1,6-heptadiynes, N,N-bis(2-propynyl)-p-toluenesulfonamide, and bis(1-phenyl-2-propynyl) ether, also undergo the cyclotrimerization with monoynes, such as ethyl propynoate, phenylacetylene, 1-decyne, and 1,2-diphenylacetylene, in a similar manner to produce the corresponding bicyclic benzene derivatives.