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

PEÑÉÑORY, ALICIA B; HEREDIA, ADRIÁN A

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY

BEILSTEIN-INSTITUT

Año: 2017 vol. 13 p. 910 - 918

1860-5397

Alkynyl selenides were synthesized by a straightforward one-pot and three-step methodology, without the need of diselenides asstarting reagents, under an oxygen atmosphere and using PEG 200 as the solvent. This procedure involves the in situ generation ofdialkyl diselenides through a K3PO4-assisted reaction of an alkyl selenocyanate obtained by a nucleophilic substitution reaction betweenKSeCN and alkyl halides. Successive reaction with terminal alkynes in the presence of t-BuOK affords the correspondingalkyl alkynyl selenide in moderate to good yields. Finally, this methodology allowed the synthesis of 2-alkylselanyl-substitutedbenzofuran and indole derivatives starting from convenient 2-substituted acetylenes.