jo8b00858_si_001.pdf (6.36 MB)
Copper-Catalyzed Sulfenylation, Sulfonylation, and Selenylation of 2,3-Allenoic Acids with Disulfides or Diselenides
journal contribution
posted on 2018-05-17, 00:00 authored by Ya-Xun Xin, Shen Pan, Yangen Huang, Xiu-Hua Xu, Feng-Ling QingThe
efficient copper-catalyzed sulfenylation and selenylation of
2,3-allenoic acids with disulfides or diselenides were developed,
respectively. These reactions proceeded through tandem radical addition/intramolecular
cyclization processes, affording a series of 4-sulfenylated and 4-selenylated
butenolides in moderate to excellent yields. Moreover, 4-sulfonylated
butenolides could also be obtained by sulfenylation of 2,3-allenoic
acids and subsequent oxidation. Further transformation of the sulfur-
and selenium-containing butenolides afforded the corresponding furan
derivatives in good yields.