Gold(I)-catalyzed rearrangement of propargyl benzyl ethers: A practical method for the generation and in situ transformation of substituted allenes

Benoit Bolte 1 Yann Odabachian 1 Fabien Gagosz 1, *
* Corresponding author
1 DCSO - Laboratoire de synthèse organique
Abstract : A series of benzyl propargyl ethers react with a gold(I) catalyst to furnish variously substituted allenes via a 1,5-hydride shift/fragmentation sequence. This transformation is rapid and practical. It can be performed under very mild conditions (room temperature or 60 °C) using terminal as well as substituted alkyne substrates bearing a primary, secondary, or tertiary benzyl ether group. The allenes thus formed can be reacted in situ with an internal or external nucleophile, corresponding to an overall reductive substitution process, to produce more functionalized compounds.
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Submitted on : Thursday, February 27, 2014 - 9:14:49 PM
Last modification on : Thursday, February 7, 2019 - 5:19:33 PM

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CNRS | X-DCSO | X | PARISTECH | INC-CNRS | X-DEP-CHIM

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Benoit Bolte, Yann Odabachian, Fabien Gagosz. Gold(I)-catalyzed rearrangement of propargyl benzyl ethers: A practical method for the generation and in situ transformation of substituted allenes. Journal of the American Chemical Society, American Chemical Society, 2010, 132 (21), pp.7294-7296. ⟨10.1021/ja1020469⟩. ⟨hal-00951251⟩

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