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. 2011 Jul 15;15(4):758-762.
doi: 10.1021/op200046v.

Rhodium-Catalyzed C-H Amination - An Enabling Method for Chemical Synthesis

J Du Bois  1
Affiliations

Rhodium-Catalyzed C-H Amination - An Enabling Method for Chemical Synthesis

J Du Bois. Org Process Res Dev. .

Abstract

Reaction methods for selective C-H amination are finding ever-increasing utility for the preparation of nitrogen-derived fine chemicals. This brief account highlights the remarkable versatility of dirhodium-based catalysts for promoting oxidation of aliphatic C-H centers in both intra- and intermolecular reaction processes.

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Figures

Figure 1
Figure 1
Heterocycle synthesis through intramolecular C–H amination.
Figure 2
Figure 2
Early examples of C–H amination using iminoiodinane reagents.
Figure 3
Figure 3
Nitrenoid C–H insertion through in situ iodoimine formation.
Figure 4
Figure 4
Stereospecific and stereoselective C–H amination with sulfamate ester substrates.
Figure 5
Figure 5
Diastereoselective Rh-catalyzed C–H insertion through a putative chair-like transition structure.
Figure 6
Figure 6
Highly selective intermolecular C–H amination reactions, as described by Dauban and Dodd; DCE = 1,2-dichloroethane.
Figure 7
Figure 7
A chiral tetra-lactamate dirhodium catalyst for enantioselective C–H amination with arylpropyl-derived sulfamates.
Figure 8
Figure 8
Optimal catalyst performance with a strapped carboxylate ligand design.
Figure 9
Figure 9
Rh2(esp)2-catalyzed intramolecular C–H amination to prepare 1,3-diamines.
Figure 10
Figure 10
Intermolecular benzylic C–H amination promoted efficiently by Rh2(esp)2.
Figure 11
Figure 11
Carbamate C–H insertion highlighted in the synthesis of the fugu toxin.
Figure 12
Figure 12
Sulfamate ester oxidation en route to complex amino acids.
Figure 13
Figure 13
Unique N,O-acetal electrophiles derived from sulfamate ester C–H amination.
See this image and copyright information in PMC

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