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Relevant academic research and scientific papers

One-step exchange-labelling of pyridines and other N-heteroaromatics using deuterium gas: catalysis by heterogeneous rhodium and ruthenium catalysts

A wide range of pyridines and other nitrogen heteroaromatics can be labelled with deuterium at room temperature and pressure by isotopic exchange with deuterium gas in THF in the presence of rhodium black, ruthenium black or 5% rhodium on alumina. The lab

C6-Selective Direct Arylation of 2-Phenylpyridine via an Activated N-methylpyridinium Salt: A Combined Experimental and Theoretical Study

An elegant pre-activation strategy, based on the formation of N-methylpyridinium iodide salts for C6-selective direct arylation of 2-phenylpyridines using Pd/Cu cooperative catalysis, has been developed. By this methodology, a wide range of unsymmetrical 2, 6-diarylpyridines were synthesized with high reactivity and regioselectivity as well as good functional group tolerance. In particular, challenging substrates bearing electron donating groups (EDGs), such as OMe, NMe2, were also successfully employed in this reaction. Deuterium incorporation studies revealed that the C?H bond acidity is improved significantly in N-methylpyridinium salts compared with their N-Oxide and N-iminopyridinium ylide counterparts, thus solving the long-standing problem associated with previous strategies for the synthesis of diaryl pyridines. Finally, the control experiments and DFT calculations supported a Pd-catalyzed and Cu-mediated mechanism in which a carbenoid copper species that is formed in-situ from N-methylpyridinium salts, participates in a Pd-catalyzed arylation followed by an iodide-promoted N-demethylation process. (Figure presented.).

Tuning up rhodium black

A new catalytic system based on rhodium black using Crabtree's catalyst as an additive for direct hydrogen isotope exchange in aromatic compounds has been investigated. The level of deuterium incorporation can be improved from 16% to 93%. The new catalyst mixture tolerates a variety of solvents. Other rhodium sources can be used, but the degree of crystallinity of the rhodium (metal, black or on support) plays an important role. Rhodium sources with a low degree of crystallinity had the highest catalytic activity. Copyright

The effect of adding Crabtree's catalyst to rhodium black in direct hydrogen isotope exchange reactions

A new catalytic system based on rhodium black using Crabtree's catalyst as an additive for direct hydrogen isotope exchange in aromatic compounds has been investigated. The level of deuterium incorporation can be improved from for example 16 to 93%. The new catalyst mixture tolerates a variety of solvents. Copyright

Scope and regiochemistry of ligand C-H activation reactions of Cp2Zr(CH3)(THF)+

The cationic complex Cp2Zr(CH3)(THF)+ (1) reacts with a series of N-heterocycles derived from pyridine via ligand substitution followed by ligand C-H activation (σ-bond metathesis). Complex 1 reacts with 2,5-dimethylpyrazi

Protonium-deuterium exchange of substituted pyridines in neutral D2O at elevated temperatures

H-D exchange of a series of pyridines 1-15, 10H-pyridinobenzothiazine (16), phenothiazine (17), and aniline has been carried out in neutral D2O at elevated temperatures.The substrates undergo selective exchange and are generally isolated in good yield.Cyanopyridines 4, 5 and 6 hydrolyze readily in D2O at elevated temperatures, and the resultant carboxylic acids decarboxylate.This reaction provides a convenient one-step route to selectively labelled pyridines.Possible mechanisms of exchange are presented.Key words: protium-deuterium exchange, substituted pyridines, temperature effect

REACTION OF TITANOCENE ALKYLS WITH PYRIDINES; A NOVEL TYPE OF CYCLOMETALLATION REACTION

Reaction of Cp2TiR (R = alkyl) with 2-substituted-pyridines and with quinolines leads to α-metallation of these ligands with formation of triangular titanocycles containing TiIII.Proof of the metallation at the α-position comes from reactions of the complexes formed with I2 and D2O/DCl which yield the corresponding iodo- and deutero-pyridine and -quinoline derivatives.Reaction of Cp2TiR with the structurally related ligand benzalaniline leads to a side-on coordinated benzalaniline complex of titanocene.Reactions of this diamagnetic complex with I2, CO2 and H2 aredescribed.