4.4 Article

On the PdCl2-catalyzed synthesis of allylic azides and allylic sulfonamides from homoallylic alcohols

Journal

TETRAHEDRON LETTERS
Volume 52, Issue 41, Pages 5217-5219

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.07.114

Keywords

Homoallylic alcohol; Isomerization; Allylic alcohol; Aminopalladation

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According to experimental and literature data, the one-pot formation of allylic azides or sulfonamides from catalytic amounts of PdCl2, homoallylic alcohols and TMSN3 or TsNH2 occurs through C=C migration followed by regioselective nucleophilic addition on the Pd-II-activated C=C bond and beta-OH elimination. (C) 2011 Elsevier Ltd. All rights reserved.

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