Compr. Heterocyclic Chem. III Vol.10 Ring Syst. with at by Katritzky A.R., et al. (eds.)

By Katritzky A.R., et al. (eds.)

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Smith, and J. F. Unsworth, J. , Perkin Trans. 2, 1974, 1004. S. Gronowitz, I. -B. Ho¨rnfeldt, Chem. , 1975, 7, 211. J. I. G. Cadogan; ‘Organophosphorus Reagents in Organic Synthesis’, Academic Press, London, 1979, p. 279. A. J. Mancuso and D. Swern, Synthesis, 1981, 165. B. M. Gimarc, J. Am. Chem. , 1983, 105, 1979. M. G. Saulnier and G. W. , 1983, 24, 5435. M. P. Cava and M. V. Lakshmikantham; in ‘Comprehensive Heterocyclic Chemistry I’, A. R. Katrizky and C. W. 4, p. 1037. 1984CHEC(6)1027 C. A.

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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