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Gold(I)-Catalyzed Rearrangement of Propargyl Benzyl Ethers: A Practical Method for the Generation and in Situ Transformation of Substituted Allenes

Benoit Bolte, Yann Odabachian and Fabien Gagosz*

*Département de Chimie, UMR 7652, CNRS/Ecole Polytechnique, 91128 Palaiseau, France, Email: gagoszdcso.polytechnique.fr

B. Bolte, Y. Odabachian, F. Gagosz, J. Am. Chem. Soc., 2010, 132, 7294-7296.

DOI: 10.1021/ja1020469 (free Supporting Information)


Abstract

Benzyl propargyl ethers react with a gold(I) catalyst to furnish substituted allenes via a 1,5-hydride shift/fragmentation sequence. This transformation is rapid and practical and can be performed under very mild conditions using terminal as well as substituted alkyne substrates bearing a primary, secondary, or tertiary benzyl ether group.

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Key Words

Allenes


ID: J48-Y2010-1560