4.4 Article

Bi(OTf)3-catalyzed allylation of quinones with allyltrimethylsilane

Journal

TETRAHEDRON LETTERS
Volume 44, Issue 26, Pages 4861-4864

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(03)01130-4

Keywords

bismuth triflate; allylation; quinones; allyl benzenes

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p-Quinones react smoothly with allyltrimethylsilane in the presence of 2 mol%, of Bi(OTf)(3) under mild reaction conditions to afford the corresponding allyl substituted benzene derivatives, p-allylquinols and allyl substituted 1,4-naphthoquinones in excellent yields with high regioselectivity. This method is very useful for the direct introduction of an allyl functionality onto a quinone moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.

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