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Issue 23, 2012
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Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent “gold rush”

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Abstract

Transition metal-catalyzed acyloxy migration of propargylic esters offers versatile entries to allene and vinyl carbene intermediates for various fascinating subsequent transformations. Most π-acidic metals (e.g. gold and platinum) are capable of facilitating these acyloxy migration events. However, very few of these processes involve redox chemistry, which are well-known for most other transition metals such as rhodium. The coupling of acyloxy migration of propargylic esters with oxidative addition, migratory insertion, and reductive elimination may lead to ample new opportunities for the design of new reactions. This tutorial review summarizes recent developments in Rh-catalyzed 1,3- and 1,2-acyloxy migration of propargylic esters in a number of cycloaddition reactions. Related Au- and Pt-catalyzed cycloadditions involving acyloxy migration are also discussed.

Graphical abstract: Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent “gold rush”

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Publication details

The article was received on 01 Jul 2012 and first published on 15 Aug 2012


Article type: Tutorial Review
DOI: 10.1039/C2CS35235D
Chem. Soc. Rev., 2012,41, 7698-7711

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    Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent “gold rush”

    X. Shu, D. Shu, C. M. Schienebeck and W. Tang, Chem. Soc. Rev., 2012, 41, 7698
    DOI: 10.1039/C2CS35235D

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