897440-09-4

Upstream product

• 1008-89-5 2-phenylpyridine 
• 109306-86-7 2-(2-Bromophenyl)pyridine 
• 98-80-6 phenylboronic acid 
• 109-04-6 2-bromo-pyridine 
• 945491-50-9 rac-(T-4)-chloro(η5-pentamethylcyclopentadienyl)(2-phenylene-κC(1'),pyridine-κN)rhodium(III) 

Downstream Products

• 897440-32-3 2-(2-bromo-6-deuterophenyl)pyridine 
• 142207-36-1 2-(2,6-dideuterophenyl)pyridine 

Relevant academic research and scientific papers

Tris-NHC-propagated self-supported polymer-based Pd catalysts for heterogeneous C-H functionalization

Three-dimensionally propagated imidazolium-containing mesoporous coordination polymer and organic polymer-based platforms were successfully exploited to develop single-site heterogenized Pd-NHC catalysts for oxidative arene/heteroarene C-H functionalization reactions. The catalysts were efficient in directed arene halogenation, and nondirected arene and heteroarene arylation reactions. High catalytic activity, excellent heterogeneity and recyclability were offered by these systems making them promising candidates in the area of heterogeneous C-H functionalization, where efficient catalysts are still scarce.

Palladium-Catalyzed Directed Halogenation of Bipyridine N-Oxides

The palladium-catalyzed directed C-H halogenation of bipyridine N-oxides was investigated. Using NCS or NBS (N-chloro- or N-bromosuccinimide) and 5 mol % Pd(OAc)2 in chlorobenzene (0.10 molar) at 110 °C, pyridine-directed functionalization took place and 3-chloro- or 3-bromobipyridine N-oxides were obtained in high yields. The reaction is sensitive to steric hindrance by 4- and 6′-substituents. Only in the latter case, where coordination of palladium by the pyridine is hindered, 3′-halogenation directed by the N-oxide function was observed. The halogenated products were deoxygenated by PCl3 or PBr3.

Directed C?H Activation and Tandem Cross-Coupling Reactions Using Palladium Nanocatalysts with Controlled Oxidation

Controlled oxidation of palladium nanoparticles provided high-valent PdIV oxo-clusters which efficiently promote directed C?H halogenation reactions. In addition, palladium nanoparticles can undergo changes in oxidation states to provide both high-valent PdIV and low-valent Pd0 species within one system, and thus a tandem reaction of C?H halogenation and cross-coupling (C?N, C?C, and C?S bond formation) was successfully established.

[Cp?RhCl2]2: Mechanosynthesis and applications in C-H bond functionalisations under ball-milling conditions

A mechanochemical synthesis of [Cp?RhCl2]2 has been developed. Under LAG conditions the organometallic complex can be prepared in a shorter reaction time compared to the standard solution-based protocol. The obtained Rh(III) dimer is then applicable as catalyst in subsequent solvent-free mechanochemical C-H bond functionalisations of 2-phenylpyridine.

Cu-mediated direct aryl C - H halogenation: A strategy to control mono- and di-selectivity

A protocol for the copper-mediated direct aryl C - H halogenation is presented. Highly selective mono- and di-halogenations are achieved by using acyl hypohalites, generated in situ from the readily available carboxylic acid and N-halosuccinimides (NXS; X=Br and Cl) as powerful halogenating reagents. The correct choice of carboxylic acid additives and solvents is essential for both high yield and selectivity. Consequently, the use of inexpensive Cu catalyst and the new strategy for the in situ generation of acyl hypohalite halogenating reagents from the readily affordable and easily-to-handle carboxylic acid and NXS (X=Br and Cl) offers advantages for practical application. Copyright

Copper-catalyzed aromatic C-H bond halogenation with lithium halides under aerobic conditions

A concise and practical Cu-catalyzed protocol for the preparation of chloro- and bromoarenes via C-H bond activation has been developed. The advantages of this strategy are the employment of cheap Cu(NO3) 2·3H2O, LiX and O2, and its compatibility with both electron-donating and electron-withdrawing substituents on aryl rings.

High-yielding, versatile, and practical [Rh(III)Cp*]-catalyzed ortho bromination and iodination of arenes

We report a uniquely high-yielding, general, and practical ortho bromination and iodination reaction of different classes of aromatic compounds. This reaction occurs by Rh(III)-catalyzed C-H bond activation methodology and is therefore the first example of the application of this cationic catalyst for C-Br and C-I bond formation.

Copper-catalyzed aromatic C-H bond halogenation using lithium halides as halogenating reagents

The copper-catalyzed C-H halogenation of 2-aryl-pyridines containing a variety of electron-withdrawing and electron-donating substituents was described. It is worth noting that cheap and easy-to-handle lithium halides were utilized as the halogen sources. Georg Thieme Verlag Stuttgart · New York.

Chelating N-heterocyclic carbene alkoxide as a supporting ligand for PdII/IV C-H bond functionalization catalysis

(Chemical Equation Presented) A PdIV complex that represents a viable catalytic intermediate in Pd-catalyzed C-H bond halogenation reactions has been isolated and structurally characterized. It contains the first examples of both a PdIV NHC bond and a PdIV alkoxide bond and serves as a precatalyst for C-H bond halogenation. As such, this represents a new class of tunable supporting ligand systems in PdIV catalysis.

Directed palladium-catalyzed oxidative C-H arylation of (hetero)arenes with arylboronic acids by using TEMPO

Oxidative coupling of three different arenes and a thiophene derivative with various arylboronic acids with Pd(OAc)2 and the commercially available 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO) as an oxidant are reported. A 2-pyridyl gro