150545-04-3Relevant academic research and scientific papers
Mild C - H halogenation of anilides and the isolation of an unusual palladium(I)-palladium(II) species
Bedford, Robin B.,Haddow, Mairi F.,Mitchell, Charlotte J.,Webster, Ruth L.
, p. 5524 - 5527 (2011/07/31)
Reducing the load: A facile palladium-catalyzed ortho-selective bromination and chlorination of anilides occurs under aerobic conditions at room temperature when N-halosuccinimides (NXS) are used in the presence of p-toluenesulfonic acid (PTSA). The orthopalladated PTSA complex is not only catalytically competent but also undergoes a reductive process to yield an unusual PdI-PdII tetramer (see structure; Pdgreen, Ored, Syellow, Cgray). Copyright
Solvent-free aromatic C-H functionalisation/halogenation reactions
Bedford, Robin B.,Engelhart, Jens U.,Haddow, Mairi F.,Mitchell, Charlotte J.,Webster, Ruth L.
, p. 10464 - 10472 (2011/01/05)
The solvent-free, palladium-catalysed reaction of anilides with CuCl 2 in the presence or absence of copper acetate yields ortho-chlorinated anilides in good to excellent yields, even on a large scale (100 mmol). By contrast, the equivalent reactions with copper bromide, either solvent free or in 1,2-dichloroethane, in the presence or absence of palladium, under air or inert conditions, gave the products of simple electrophilic bromination. Mechanistic studies highlighted the involvement of palladacyclic intermediates, one of which was characterised crystallographically, which undergo subsequent reaction with copper(ii) chloride to yield the chlorinated anilide products.
Solvent free catalytic C-H functionalisation
Bedford, Robin B.,Mitchell, Charlotte J.,Webster, Ruth L.
scheme or table, p. 3095 - 3097 (2010/08/04)
Solvent-free reaction conditions facilitate a range of aromatic C-H functionalisations that traditionally require acidic or disfavoured solvents. These reactions include selective ortho- and meta-arylation of aryl carbamates and anilides and selective halogenation reactions. The Royal Society of Chemistry 2010.
Scope and selectivity in palladium-catalyzed directed C-H bond halogenation reactions
Kalyani, Dipannita,Dick, Allison R.,Anani, Waseem Q.,Sanford, Melanie S.
, p. 11483 - 11498 (2007/10/03)
Palladium-catalyzed ligand directed C-H activation/halogenation reactions have been extensively explored. Both the nature of the?directing group and the substitution pattern on the arene ring of the substrate lead to different reactivity profiles, and often different and complementary products, in the presence and absence of the catalyst.
Conformational Analysis of Crowded Anilides and Thioanilides. The "En-Face" Steric Effect of Aryl Groups
Pettersson,Ingrid,Sandstroem, Jan
, p. 397 - 406 (2007/10/02)
In order to study the interaction of isobutyl, neopentyl, and isopropyl groups with the "face" of aromatic rings, a series of o,o'-disubstituted anilides and thioanilides with the above-mentioned groups as N-substituents has been investigated by temperatu
