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Improvement in the synthesis of (Z)-organylthioenynes via hydrothiolation of buta-1,3-diynes: a comparative study using NaOH or TBAOH as base

2012; Elsevier BV; Volume: 53; Issue: 43 Linguagem: Inglês

10.1016/j.tetlet.2012.08.003

1873-3581

Amanda S. Santana, Diego B. Carvalho, Nadla S. Casemiro, Gabriela R. Hurtado, Luíz Henrique Viana, Nájla Mohamad Kassab, Sandro L. Barbosa, Francisco A. Marques, Palimécio G. Guerrero, Adriano C. M. Baroni,

Synthesis of heterocyclic compounds

Hydrothiolation of symmetrical and unsymmetrical buta-1,3-diynes with sodium organylthiolate anions in reflux, generated in situ by reacting C4H9SH with NaOH, afforded (Z)-organylthioenynes in low to good yields (25–80%). By using tetrabutylammonium hydroxide (TBAOH) as base instead of NaOH, the hydrothiolation of buta-1,3-diynes was more rapid and efficient, providing (Z)-organylthioenynes in good to excellent yields (70–95%).