Guiding principles for site selective and stereoselective intermolecular C-H functionalization by donor/acceptor rhodium carbenes.

Guiding principles for site selective and stereoselective intermolecular C-H functionalization by donor/acceptor rhodium carbenes.

Chemical Society reviews (2011-03-02)

Huw M L Davies, Daniel Morton

ABSTRACT

This tutorial review presents a description of the controlling elements of intermolecular C-H functionalization by means of C-H insertion by donor/acceptor rhodium carbenes. These rhodium carbenes, readily derived from the combination of diazo compounds with dirhodium(ii) catalysts, are sufficiently reactive to undergo a wide range of C-H insertions. They are also capable of highly selective reactions, controlled by a combination of steric and electronic factors. An overview of the structural factors that influence site selectivity will be given, followed by a description of the exceptional diastereo- and enantioselectivity that can be achieved. Several examples will be shown of how this methodology can be applied to streamline the synthesis of natural products and pharmaceutical targets.

MATERIALS

Product Number

Brand

Product Description

204218

Sigma-Aldrich

Rhodium, powder, 99.95% trace metals basis

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%

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%