Journal
TETRAHEDRON LETTERS
Volume 50, Issue 27, Pages 3801-3804Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.04.030
Keywords
Baylis-Hillman adducts; Ionic liquids; Hypervalent iodine; Oxidation; Sulfides; Regioselective synthesis
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The first example of tandem oxidation and 1,2-acetoxysulfenylation/1,2-disulfenylation of Baylis-Hillman (BH) alcohols to afford 1,2-acetoxysulfides/1,2-dithioethers is reported. The reaction involves oxidation of BH alcohols with IBX in [bmim]Br to give beta-ketomethylene compounds in situ followed by CuI-imidazole-catalyzed 1,2-acetoxysulfenylation with an organodisulfide and acetic acid under air to afford vicinal acetoxysulfides in excellent yields with complete regioselectivity. In the absence of the Cu(I) catalyst, 1,2-disulfenylation takes place to give vicinal dithioethers in 81-90% yields. (C) 2009 Elsevier Ltd. All rights reserved.
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