60263-44-7

Upstream product

• 110-86-1 pyridine 
• 15672-98-7 3,3-dimethyl-butylmercury ⁽¹⁺⁾; chloride 
• 938764-42-2 2-(3,3-dimethylbutyl)-6-(triisopropylsilyl)pyridine 
• 677-22-5 tert-butylmagnesium chloride 
• 22320-32-7 2-(2-pyridinyl)-ethyl 4-methylbenzenesulfonate 
• 766-77-8 Dimethylphenylsilane 
• 558-37-2 tert-butylethylene 
• 100-69-6 2-vinylpyridine 
• 507-19-7 t-butyl bromide 
• 938764-49-9 2-(triisopropylsilyl)pyridine 
• 109-04-6 2-bromo-pyridine 

Relevant academic research and scientific papers

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.

C2-Selective silylation of pyridines by a rhodium-aluminum complex

We have developed a C2-selective mono-silylation of a variety of pyridines using a Rh-Al complex. Both the site- and mono-selectivity are controlledviathe pyridine coordination to the Lewis-acidic Al center prior to the activation of the pyridine C(2)-H bond at the proximal Rh center. A reaction mechanism is proposed based on several mechanistic studies, including the isolation of a (2-pyridyl)silylrhodium intermediate.

Fe-Catalyzed Reductive Couplings of Terminal (Hetero)Aryl Alkenes and Alkyl Halides under Aqueous Micellar Conditions

The combination of a vinyl-substituted aromatic or heteroaromatic and an alkyl bromide or iodide leads, in the presence of Zn and a catalytic amount of an Fe(II) salt, to a net reductive coupling. The new C-C bond is regiospecifically formed at rt at the β-site of the alkene. The coupling only occurs in an aqueous micellar medium, where a radical process is likely, supported by several control experiments. A mechanism based on these data is proposed.

Copper-catalyzed cross-coupling of functionalized alkyl halides and tosylates with secondary and tertiary alkyl Grignard reagents

Added value: A copper-based method is highly efficient for the cross-coupling of alkyl electrophiles with secondary and tertiary alkyl Grignard reagents. The method is distinguished by its broad substrate scope and high functional group tolerance. Copyright

Rh(I)-catalyzed alkylation of quinolines and pyridines via C-H bond activation

The scope of heterocycle ortho-alkylation has been dramatically expanded to include pharmaceutically important pyridines and quinolines, which contain only a single nitrogen. The reactions, which are conducted at a high concentration (0.8 M), can be performed with catalyst loadings as low as 1% Rh. Substitution ortho to the heterocycle ring nitrogen is required for efficient alkylation and is consistent with the intermediacy of a Rh-carbene intermediate similar to those proposed in our earlier work. Copyright

Alkylation of Pyridine in Free Radical Chain Reactions Utilizing Alkylmercurials

Pyridines or N,N,N',N'-tetramethyl-p-phenylenediamine will undergo a photostimulated free radical chain reaction with alkylmercury halides or carboxylates, yielding ring alkylated substitution products.Alkene mercuration products (R1CH(Y)CH(R2)HgX with Y=HO, RO, CH3CONH; X=Cl, CH3CO2, CF3CO2) can be used without isolation for the alkylation reaction