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Application of Ynamides in the Synthesis of 2-(Tosylamido)- and 2,5-Bis(tosylamido)thiophenes

Abstract : A step-economic and metal-catalyst-free synthesis of 2-(tosylamido)- and 2,5-bis(tosylamido)-thiophenes from nonsymmetrical 1,3-butadiynamides and symmetrical 1,3-butadiyne-1,4-diamides is reported. The reaction proceeds in the presence of Na2S·9H2O (2–3 equiv) under mild reaction conditions (50 °C) and is facilitated by polarized carbon–carbon triple bonds in ynamides. This new approach to thiophenes based on the chemistry of ynamides was applied to the synthesis of a bis(tosylamido)-capped terthiophene having a string of N,S-heteroatoms embedded in a highly π-conjugated molecular frame.
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Imen Talbi, Carole Alayrac, Jean-François Lohier, Soufiane Touil, Bernhard Witulski. Application of Ynamides in the Synthesis of 2-(Tosylamido)- and 2,5-Bis(tosylamido)thiophenes. Organic Letters, American Chemical Society, 2016, 18 (11), pp.2656 - 2659. ⟨10.1021/acs.orglett.6b01101⟩. ⟨hal-01834440⟩



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