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  • 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
PMID21359404
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
GF37207166
Rhodium, wire reel, 0.1m, diameter 1.0mm, as drawn, 99.9%
GF71687357
Rhodium, microfoil, disks, 10mm, thinness 0.1Ī¼m, specific density 124Ī¼g/cm2, permanent mylar 3.5Ī¼m support, 99.9%
GF49036204
Rhodium, foil, not light tested, 25x25mm, thickness 0.00075mm, permanent polyester support, 99.85%
GF83497652
Rhodium, wire reel, 0.05m, diameter 1.0mm, as drawn, 99.9%
GF38835737
Rhodium, wire reel, 0.2m, diameter 0.12mm, as drawn, 99.9%
GF72510364
Rhodium, wire reel, 0.5m, diameter 0.25mm, hard, 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%
GF17496973
Rhodium, wire reel, 0.2m, diameter 0.5mm, as drawn, 99.9%
GF54466937
Rhodium, wire reel, 0.5m, diameter 0.12mm, as drawn, 99.9%
GF37380089
Rhodium, wire reel, 0.2m, diameter 0.25mm, hard, 99.9%
GF49946417
Rhodium, microfoil, disks, 10mm, thinness 0.50Ī¼m, specific density 620Ī¼g/cm2, permanent mylar 3.5Ī¼m support, 99.99%
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%
GF14938005
Rhodium, microfoil, disks, 25mm, thinness 0.1Ī¼m, specific density 124Ī¼g/cm2, permanent mylar 3.5Ī¼m support, 99.9%
GF24911726
Rhodium, foil, not light tested, 25x25mm, thickness 0.012mm, as rolled, 99.9%
GF57675561
Rhodium, foil, light tested, 25x25mm, thickness 0.05mm, as rolled, 99.9%
GF82366342
Rhodium, foil, not light tested, 50x50mm, thickness 0.00025mm, permanent polyester support, 99.9%
GF64213680
Rhodium, wire reel, 0.05m, diameter 0.12mm, as drawn, 99.9%
GF12568013
Rhodium, foil, light tested, 25x25mm, thickness 0.05mm, as rolled, x-ray quality, 99.9%
GF45819995
Rhodium, wire reel, 0.05m, diameter 0.25mm, hard, 99.9%
GF96356559
Rhodium, foil, light tested, 25x25mm, thickness 0.075mm, 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%
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%
GF33789550
Rhodium, foil, not light tested, 50x50mm, thickness 0.001mm, permanent polyester support, 99.85%
GF80841146
Rhodium, foil, 25x25mm, thickness 0.15mm, as rolled, 99.9%