Iridium-catalyzed direct C-H amidation with weakly coordinating carbonyl directing groups under mild conditions.

@article{Kim2014IridiumcatalyzedDC,
  title={Iridium-catalyzed direct C-H amidation with weakly coordinating carbonyl directing groups under mild conditions.},
  author={Jinwoo Kim and Sukbok Chang},
  journal={Angewandte Chemie},
  year={2014},
  volume={53 8},
  pages={
          2203-7
        }
}
An iridium-catalyzed direct C-H amidation of weakly coordinating substrates, in particular of those bearing ester and ketone groups, under very mild conditions has been developed. The observed high reaction efficiency was achieved by the combined use of acetic acid and lithium carbonate as additives. 
178 Citations
Iridium‐Catalyzed Direct C—H Amidation with Weakly Coordinating Carbonyl Directing Groups under Mild Conditions.
Aromatic ketones and esters are directly amidated under mild conditions using an iridium catalyst combined with acetic acid and lithium carbonate as additives.
Iridium-catalyzed direct ortho -C-H amidation of benzoic acids with sulfonylazides
Abstract A mild and efficient iridium-catalyzed ortho-C H amidation with sulfonyl azides by weakly coordinating carboxylic acid was demonstrated, which provided a novel approach to anthranilic acidExpand
Iridium(III)-catalyzed C-H amidation of arylphosphoryls leading to a P-stereogenic center.
TLDR
Direct CH amidation of arylphosphoryl compounds has been developed by using an Ir(III) catalyst system under mild conditions and was successfully applied for the first time to the asymmetric reaction giving rise to a P-chirogenic center. Expand
Iridium-catalyzed C-H amination with anilines at room temperature: compatibility of iridacycles with external oxidants.
Described herein is the development of an iridium-catalyzed direct C-H amination of benzamides with anilines at room temperature, representing a unique example of an Ir catalyst system that isExpand
Rhodium-Catalyzed Direct Ortho C-H Arylation Using Ketone as Directing Group with Boron Reagent.
A general method for selective ortho C-H arylation of ketone, with boron reagent enabled by rhodium complexes with excellent yields, is developed. The transformation is characterized by the use ofExpand
Cobalt(III)-Catalyzed C–H Amidation of Arenes using Acetoxycarbamates as Convenient Amino Sources under Mild Conditions
The Co(III)-catalyzed direct C–H amidation of arenes has been developed using O-acylcarbamates as a convenient amino source. This reaction proceeded in high efficiency under external oxidant-freeExpand
Iridium-Catalyzed Direct ortho-C-H Amidation of Benzaldehydes through N-Sulfonyl Imines as Mask.
TLDR
A series of ortho-amided benzaldehydes were obtained in up to 95% yields for 21 examples with excellent regioselectivity and broad functional group tolerance, providing an environmentally benign sulfamidation process. Expand
Iridium-catalyzed direct C-H amidation of anilines with sulfonyl azides: easy access to 1,2-diaminobenzenes.
TLDR
The developed protocol has good compatibility with diverse functional groups, efficiently providing the monoamidated products with good to excellent yields under mild reaction conditions and offering the synthetically useful 1,2-diaminobenzene scaffold. Expand
Copper-catalyzed C(sp2)-H amidation with azides as amino sources.
TLDR
A copper-catalyzed C-H amidation process, with azides as amino sources under oxidant-free conditions, has been developed and tandem C-N/N-N bond formation occurred to afford indazole derivatives in one pot. Expand
Pd-Catalyzed Direct ortho-C-H Arylation of Aromatic Ketones Enabled by a Transient Directing Group.
TLDR
The ketimine/carboxylate bidentate directing group in situ generated from aromatic ketone and glycine enabled a palladium-catalyzed ortho-C-H arylation, which shows extensive substrate compatibility. Expand
...
1
2
3
4
5
...

References

SHOWING 1-10 OF 55 REFERENCES
Iridium-catalyzed direct arene C-H bond amidation with sulfonyl- and aryl azides.
TLDR
Iridium-catalyzed direct ortho C-H amidation of arenes has been shown to work well with sulfonyl- and aryl azides as the nitrogen source and with a broad range of substrates bearing conventional directing groups with excellent functional group compatibility under mild conditions. Expand
Ruthenium-catalyzed direct C-H amidation of arenes including weakly coordinating aromatic ketones.
C-H activation: The ruthenium-catalyzed direct sp(2) C-H amidation of arenes by using sulfonyl azides as the amino source is presented (see scheme). A wide range of substrates were readily amidatedExpand
Rhodium(III)-catalyzed intermolecular N-chelator-directed aromatic C-H amidation with amides.
TLDR
Rh(III)-catalyzed intermolecular direct aromatic C-H bond amidation with amides has been accomplished under mild reaction conditions and a possible mechanism is proposed according to the experimental results. Expand
Rhodium-catalyzed direct C-H amination of benzamides with aryl azides: a synthetic route to diarylamines.
TLDR
A rhodium-catalyzed direct intermolecular C-H amination of benzamides and ketoximes using aryl azides as the amine source has been developed and produces diarylamines in high yields. Expand
Rhodium-catalyzed intermolecular amidation of arenes with sulfonyl azides via chelation-assisted C-H bond activation.
TLDR
A broad range of chelate group-containing arenes are selectively amidated with excellent functional group tolerance, thus opening a new avenue to practical intermolecular C-N bond formation. Expand
Oxidative alkenylation of aromatic esters by ruthenium-catalyzed twofold C-H bond cleavages.
TLDR
The oxidative Fujiwara-Moritani-type alkenylation provided step-economical access to diversely substituted styrenes and proved viable in an aerobic manner. Expand
Intramolecular Ir(I)-catalyzed benzylic C-H bond amination of ortho-substituted aryl azides.
Iridium(I) catalyzes the intramolecular benzylic C-H bond amination of ortho-homobenzyl-substituted aryl azides to produce indolines at 25 degrees C.
Rhodium-catalyzed selective olefination of arene esters via C-H bond activation.
TLDR
Ester and carboxaldehyde units were revealed to be effective chelating groups in focusing the activation of aryl C-H bonds ortho to the directing moieties under the Rh-catalyzed oxidative conditions. Expand
Ruthenium(II)-catalyzed synthesis of hydroxylated arenes with ester as an effective directing group.
An unprecedented Ru(II) catalyzed ortho-hydroxylation has been developed for the facile synthesis of a variety of multifunctionalized arenes from easily accessible ethyl benzoates with ester as anExpand
Directed ortho borylation of functionalized arenes catalyzed by a silica-supported compact phosphine-iridium system.
An immobilized monophosphine-Ir system, which was prepared in situ from [Ir(OMe)(cod)](2) and a silica-supported, compact phosphine, showed high activities and selectivities for the borylation ofExpand
...
1
2
3
4
5
...