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

ZUSAMMENFASSUNG

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.

MATERIALIEN

Produktnummer

Marke

Produktbeschreibung

204218

Sigma-Aldrich

Rhodium, powder, 99.95% trace metals basis

GF80841146

Rhodium, foil, 25x25mm, thickness 0.15mm, as rolled, 99.9%

GF74452316

Rhodium, wire reel, 0.05m, diameter 0.5mm, as drawn, 99.9%

GF57675561

Rhodium, foil, light tested, 25x25mm, thickness 0.05mm, as rolled, 99.9%

GF44569907

Rhodium, foil, 25x25mm, thickness 0.125mm, as rolled, 99.9%

GF40539405

Rhodium, foil, 25x25mm, thickness 0.1mm, as rolled, 99.9%

GF72510364

Rhodium, wire reel, 0.5m, diameter 0.25mm, hard, 99.9%

GF45819995

Rhodium, wire reel, 0.05m, diameter 0.25mm, hard, 99.9%

GF15499413

Rhodium, foil, not light tested, 25x25mm, thickness 0.006mm, as rolled, 99.9%

GF49946417

Rhodium, microfoil, disks, 10mm, thinness 0.50μm, specific density 620μg/cm², permanent mylar 3.5μm support, 99.99%

GF35442727

Rhodium, foil, not light tested, 25x25mm, thickness 0.0005mm, permanent polyester support, 99.85%

GF71687357

Rhodium, microfoil, disks, 10mm, thinness 0.1μm, specific density 124μg/cm², permanent mylar 3.5μm support, 99.9%

GF14938005

Rhodium, microfoil, disks, 25mm, thinness 0.1μm, specific density 124μg/cm², permanent mylar 3.5μm support, 99.9%

GF37207166

Rhodium, wire reel, 0.1m, diameter 1.0mm, as drawn, 99.9%

GF12568013

Rhodium, foil, light tested, 25x25mm, thickness 0.05mm, as rolled, x-ray quality, 99.9%

GF04978963

Rhodium, foil, not light tested, 10x10mm, thickness 0.012mm, as rolled, 99.9%

GF87742659

Rhodium, foil, not light tested, 25x25mm, thickness 0.001mm, permanent polyester support, 99.85%

GF22634120

Rhodium, foil, not light tested, 50x50mm, thickness 0.00075mm, permanent polyester support, 99.85%

GF96356559

Rhodium, foil, light tested, 25x25mm, thickness 0.075mm, as rolled, 99.9%

GF49036204

Rhodium, foil, not light tested, 25x25mm, thickness 0.00075mm, permanent polyester support, 99.85%

GF33789550

Rhodium, foil, not light tested, 50x50mm, thickness 0.001mm, permanent polyester support, 99.85%

GF36379345

Rhodium, foil, light tested, 15x15mm, thickness 0.05mm, as rolled, 99.9%

GF24911726

Rhodium, foil, not light tested, 25x25mm, thickness 0.012mm, as rolled, 99.9%

GF64213680

Rhodium, wire reel, 0.05m, diameter 0.12mm, as drawn, 99.9%

GF26710680

Rhodium, wire reel, 0.1m, diameter 0.12mm, as drawn, 99.9%

GF27499045

Rhodium, wire reel, 0.1m, diameter 0.25mm, hard, 99.9%

GF37380089

Rhodium, wire reel, 0.2m, diameter 0.25mm, hard, 99.9%

GF54466937

Rhodium, wire reel, 0.5m, diameter 0.12mm, as drawn, 99.9%

GF17496973

Rhodium, wire reel, 0.2m, diameter 0.5mm, as drawn, 99.9%

GF83497652

Rhodium, wire reel, 0.05m, diameter 1.0mm, as drawn, 99.9%