Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions

• Adrián A. Heredia and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2017, 13, 910–918, doi:10.3762/bjoc.13.92

• halides. Successive reaction with terminal alkynes in the presence of t-BuOK affords the corresponding alkyl alkynyl selenide in moderate to good yields. Finally, this methodology allowed the synthesis of 2-alkylselanyl-substituted benzofuran and indole derivatives starting from convenient 2-substituted

• acetylenes. Keywords: alkynyl selenide; electrophilic cyclization; nucleophilic substitution; potassium selenocyanate; terminal alkynes; Introduction Alkynyl selenides, as many other selenium compounds, have potential anti-oxidant activities, and may play a role in certain diseases such as cancer, heart

• styryl selenide 1. During optimization of the reaction conditions to 1 and in the presence of only t-BuOK, the corresponding alkynyl selenide 5 was obtained together with dialkyl selenides R2Se and R2Se2. In view of the important synthetic application of alkynyl selenides, we envisioned the possibility