Cyclotrimerization of Terminal Alkynes Catalyzed by a Phosphine‐Free Chloro(1,5‐cyclooctadiene)iridium(I) Dimer and Induced by Tin(II) Chloride

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<jats:title>Abstract</jats:title><jats:p>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)]<jats:sub>2</jats:sub>) 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, <jats:italic>N</jats:italic>,<jats:italic>N</jats:italic>‐bis(2‐propynyl)‐<jats:italic>p</jats:italic>‐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.</jats:p>

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