By Katritzky A.R., et al. (eds.)
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Extra resources for Compr. Heterocyclic Chem. III Vol.10 Ring Syst. with at least Two Fused Heterocyclic Five- or Six-memb. Rings, no Bridgehead
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This versatile synthetic route to diheteropentalenes 20, 26, 38, and 439–441 from dihalothiophenes involves Sonogashira cross-coupling reaction of 3-bromo-4-iodothiophene 434 with trimethylsilylethyne giving 435 (Scheme 51). The ethynyl compound 435 was hydroaluminated with DIBAL-H followed by bromination with NBS to give dibromo derivate 436. Treatment of 436 with t-BuLi in dry ether at À80 C, then with a suitable reagent (PhSO2)2S, (PhSO2)2Se, TeCl4, PhPCl2, PhAsCl2, or PhSbCl2), resulted in ring closure forming the 2-trimethylsilylhetero[2,3-c]thiophenes 438, presumably via key 1,4-dilithium intermediate 437.
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