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

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.

MATERIALS

Product Number

Brand

Product Description

GF36379345

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

GF15499413

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

GF27499045

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

GF14938005

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

GF57675561

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

GF64213680

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

GF24911726

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

GF38835737

Rhodium, wire reel, 0.2m, diameter 0.12mm, as drawn, 99.9%

GF45819995

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

GF82366342

Rhodium, foil, not light tested, 50x50mm, thickness 0.00025mm, permanent polyester support, 99.9%

GF22634120

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

GF44569907

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

GF74452316

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

GF04978963

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

GF17496973

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

GF33789550

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

GF17514312

Rhodium, foil, not light tested, 25x25mm, thickness 0.00025mm, permanent polyester support, 99.9%

GF96356559

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

GF06539979

Rhodium, wire reel, 0.1m, diameter 0.5mm, as drawn, 99.9%

GF37380089

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

GF81993910

Rhodium, foil, not light tested, 50x50mm, thickness 0.006mm, as rolled, 99.9%

GF35442727

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

GF80841146

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

GF54466937

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

GF83497652

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

GF87742659

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