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  • Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent "gold rush".

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

Chemical Society reviews (2012-08-17)
Xing-Zhong Shu, Dongxu Shu, Casi M Schienebeck, Weiping Tang
RESUMO

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.

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Sigma-Aldrich
Rhodium, powder, 99.95% trace metals basis
Rhodium, wire reel, 0.1m, diameter 0.5mm, as drawn, 99.9%
Rhodium, foil, 25x25mm, thickness 0.125mm, as rolled, 99.9%
Rhodium, foil, 25x25mm, thickness 0.15mm, as rolled, 99.9%
Rhodium, foil, 25x25mm, thickness 0.1mm, as rolled, 99.9%
Rhodium, foil, 12mm disks, thickness 0.5mm, as rolled, 99.9%
Rhodium, foil, light tested, 15x15mm, thickness 0.05mm, as rolled, 99.9%
Rhodium, foil, light tested, 25x25mm, thickness 0.05mm, as rolled, 99.9%
Rhodium, foil, light tested, 25x25mm, thickness 0.05mm, as rolled, x-ray quality, 99.9%
Rhodium, foil, light tested, 25x25mm, thickness 0.075mm, as rolled, 99.9%
Rhodium, foil, not light tested, 10x10mm, thickness 0.012mm, as rolled, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.00025mm, permanent polyester support, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.0005mm, permanent polyester support, 99.85%
Rhodium, foil, not light tested, 25x25mm, thickness 0.00075mm, permanent polyester support, 99.85%
Rhodium, foil, not light tested, 25x25mm, thickness 0.001mm, permanent polyester support, 99.85%
Rhodium, foil, not light tested, 25x25mm, thickness 0.006mm, as rolled, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.012mm, as rolled, 99.9%
Rhodium, foil, not light tested, 50x50mm, thickness 0.00025mm, permanent polyester support, 99.9%
Rhodium, foil, not light tested, 50x50mm, thickness 0.00075mm, permanent polyester support, 99.85%
Rhodium, foil, not light tested, 50x50mm, thickness 0.001mm, permanent polyester support, 99.85%
Rhodium, foil, not light tested, 50x50mm, thickness 0.006mm, as rolled, 99.9%
Rhodium, microfoil, disks, 10mm, thinness 0.1μm, specific density 124μg/cm2, permanent mylar 3.5μm support, 99.9%
Rhodium, microfoil, disks, 10mm, thinness 0.25μm, specific density 310μg/cm2, permanent mylar 3.5μm support, 99.99%
Rhodium, microfoil, disks, 10mm, thinness 0.50μm, specific density 620μg/cm2, permanent mylar 3.5μm support, 99.99%
Rhodium, microfoil, disks, 25mm, thinness 0.1μm, specific density 124μg/cm2, permanent mylar 3.5μm support, 99.9%
Rhodium, microfoil, disks, 25mm, thinness 0.25μm, specific density 310μg/cm2, permanent mylar 3.5μm support, 99.99%
Rhodium, wire reel, 0.05m, diameter 0.12mm, as drawn, 99.9%
Rhodium, wire reel, 0.05m, diameter 0.25mm, hard, 99.9%
Rhodium, wire reel, 0.05m, diameter 0.5mm, as drawn, 99.9%
Rhodium, wire reel, 0.05m, diameter 1.0mm, as drawn, 99.9%