36995-65-0

Upstream product

• 100-71-0 2-Ethylpyridine 
• 624-31-7 4-tolyl iodide 
• 110-86-1 pyridine 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 5084-80-0 tri(4-tolyl)boroxine 
• 100-69-6 2-vinylpyridine 
• 106-38-7 para-bromotoluene 

Relevant academic research and scientific papers

Catalytic coupling of C-H and C-I bonds using pyridine as a directing group

(Chemical Equation Presented) A method for the palladium-catalyzed arylation of pyridines and pyrazoles has been developed. Both aliphatic and aromatic C-H bonds may be functionalized using this method. A bromo substituent is tolerated on the aryl iodide coupling component.

C2-selective alkylation of pyridines by rhodium–aluminum complexes

A C2- and mono-selective alkylation of various pyridines and azines with unactivated alkenes and vinylarenes using a heterobimetallic Rh–Al catalyst is reported. The use of aliphatic alkenes exclusively affords the linear alkylation products, while vinylarenes mainly afford branched alkylation products. The details of the reaction mechanism are revealed by DFT calculations: the reductive elimination of the products is rate-determining, which is consistent with the experimental results. The origin of the linear/branched selectivity is elucidated based on deformation/interaction analysis.

"bulky-Yet-Flexible" α-Diimine Palladium-Catalyzed Reductive Heck Cross-Coupling: Highly Anti-Markovnikov-Selective Hydroarylation of Alkene in Air

To pursue a highly regioselective and efficient reductive Heck reaction, a series of moisture-and air-stable α-diimine palladium precatalysts were rationally designed, readily synthesized, and fully characterized. The relationship between the structures of the palladium complexes and the catalytic properties was investigated. It was revealed that the"bulky-yet-flexible"palladium complexes allowed highly anti-Markovnikov-selective hydroarylation of alkenes with (hetero)aryl bromides under aerobic conditions. Further synthetic application of the present protocol could provide rapid and straightforward access to functional and biologically active molecules.

Iridium(III)-Catalyzed Direct Arylation of C-H Bonds with Diaryliodonium Salts

By developing a new Ir(III)-catalyzed C-C cross-coupling, a versatile method for direct arylation of sp2 and sp3 C-H bonds in ketoximes, nitrogen-containing heterocycles, various arenes, and olefins has been established. The key to this arylation depends on the appropriate choice of catalyst and the use of diaryliodonium triflate salts as the coupling partners. This transformation has good functional group compatibility and can serve as a powerful synthetic tool for late-stage C-H arylation of complex compounds. Mechanistic studies by density functional theory calculations suggested that the sp3 C-H activation was realized by a triflate-involved concerted metalation-deprotonation process, and the following oxidation of Ir(III) to Ir(V) is the most favorable when a bistriflimide is contained in the diaryliodonium salt. Calculations indicated that both steps are enabled by initial anion exchange between the reactant complexes.

CpRhIII-Catalyzed Arylation of C(sp3) Bonds

The first CpRhIII-catalyzed arylation of unactivated C(sp3) bonds is presented. The unactivated primary C(sp3) bond of 2-alkylpyridines can be activated by RhIII and further reacts with triarylboroxines to efficiently build new C(sp3)-aryl bonds. The methodology also provides a facile and efficient synthesis of unsymmetrical triarylmethanes by RhIII-catalyzed C(sp3) arylation of diarylmethanes. Unactivated! The unactivated primary C(sp3) bond of 2-alkylpyridines can be activated by RhIII and then react with triarylboroxines to efficiently build new C(sp3)-aryl bonds (see scheme, DG=directing group, FG=functional group). The methodology also provides a facile and efficient synthesis of unsymmetrical triarylmethanes by RhIII-catalyzed C(sp3) arylation.