105664-48-0

Upstream product

• 4165-57-5 bromobenzene-d5 
• 525598-50-9 C₈H₆⁽²⁾H₅BO₂ 
• 109-04-6 2-bromo-pyridine 
• 98-98-6 2-Picolinic acid 
• 1076-43-3 benzene-d6 
• 41122-56-9 sodium 2-pyridine diazotate 
• 64-19-7 acetic acid 
• 84783-81-3 phenylmagnesium bromide-d5 
• 109-09-1 2-chloropyridine 
• 215527-70-1 2,3,4,5,6-pentadeuteriumbenzeneboronic acid 
• 694-59-7 pyridine N-oxide 

Downstream Products

• 1024585-97-4 2-(4'-tert-butyl-3,4,5,6-tetradeuteriobiphenyl-2-yl)pyridine 
• 1625-91-8 4,4'-di-tert-butylbiphenyl 
• 1046154-33-9 C₁₇H₁₄⁽²⁾H₃N 
• 1046154-31-7 C₁₇H₁₃⁽²⁾H₄N 
• 1046154-29-3 C₁₇H₁₂⁽²⁾H₅N 
• 1046154-39-5 C₂₃H₂₂⁽²⁾H₃N 
• 1046154-37-3 C₂₃H₂₁⁽²⁾H₄N 
• 1046154-35-1 C₂₃H₂₀⁽²⁾H₅N 
• 1046154-17-9 C₁₁H₅⁽²⁾H₄N 
• 1240786-97-3 (E)-2-(2-(oct-4-en-4-yl)phenyl)pyridine 
• 1240786-99-5 2-(4-methoxy-2,6-di((E)-oct-4-en-4-yl)phenyl)pyridine 
• 1251668-31-1 C₁₈H₁₁⁽²⁾H₄NO 
• 10107-60-5 1,4-diphenyl-4-vinylcyclohex-1-ene 
• 29180-91-4 1-phenyl-4-(1-phenylvinyl)cyclohex-1-ene 

Relevant academic research and scientific papers

Mechanistic Insight into Catalytic Redox-Neutral C-H Bond Activation Involving Manganese(I) Carbonyls: Catalyst Activation, Turnover, and Deactivation Pathways Reveal an Intricate Network of Steps

Manganese(I) carbonyl-catalyzed C-H bond functionalization of 2-phenylpyridine and related compounds containing suitable metal directing groups has recently emerged as a potentially useful synthetic methodology for the introduction of various groups to th

Ruthenium-catalyzed C-H allylation of arenes with allylic amines

The Ru-catalyzed pyridyl-directed C-H allylation of arenes with allylic amines has been developed. This reaction was carried out in the presence of 5 mol% of [Ru(p-cymene)Cl2]2 and 0.5 equiv. of AgOAc in CF3CH2O

RhIII-catalyzed C-H activation: A versatile route towards various polycyclic pyridinium salts

An efficient and convenient method for the synthesis of highly substituted polycyclic pyridinium salts from the reaction of various 2-aryl-pyr-idines and 2-aryl-sp2-nitrogen-atom-containing heterocycles with alkynes through rhodium(III)-catalyzed C-H activation and annulation under an O2 atmosphere is described. A possible mechanism that involves the chelation-assisted C-H activation of the 2-arylpyridine substrate, insertion of the alkyne, and reductive elimination is proposed. This mechanism was supported by the isolation of a five-mem-bered rhodacycle (I'). In addition, kinetic isotope studies were performed to understand the intimate reaction mechanism.

Rhodium(iii) vs. cobalt(iii): a mechanistically distinct three-component C-H bond addition cascade using a Cp*RhIII catalyst

Three-component C-H bond additions across two different coupling partners remain underdeveloped. Herein, we report the first three-component RhIII-catalyzed C-H bond additions to a wide range of dienes and aldehydes. Our method constitutes a complementary access with Ellman's CoIII-catalytic system to homoallylic alcohols.

Arylation/Intramolecular Conjugate Addition of 1,6-Enynes Enabled by Manganese(I)-Catalyzed C-H Bond Activation

An arylation/intramolecular conjugate addition of cyclohexadienone-containing 1,6-enynes has been established through initiation by manganese(I)-catalyzed C-H bond activation. This tandem reaction involved unusual E/Z-isomerized alkenyl-Mn intermediates and proceeded smoothly with high chemoselectivities and perfect atom economy. The cyclization products could be further transformed to various structures. Mechanistic studies suggested that cleavage of the C-H bond was involved in the turnover-limiting step, and a manganese carbene anion intermediate was proposed to explain such an E/Z isomerization process.

Ru-Catalyzed Meta-C-H Benzylation of Arenes with Toluene Derivatives

The Ru-catalyzed meta-C-H benzylation of arenes bearing pyridyl, pyrimidyl, and pyrazolyl directing groups with toluene derivatives has been reported. Heptafluoroisopropyl iodide (iC3F7I) was employed as both a mild oxidant and radical initiator. This reaction showed excellent site-selectivity and tolerated a wide range of functional groups, providing a new strategy for the synthesis of various diarylmethane moieties.

Preparation of 3,2'-Annelated 2-Phenylpyridines and Their Cyclopalladation Chemistry

A series of 3,2'-polymethylene-bridged derivatives of 2-phenylpyridine has been prepared by thermolysis of O-allyloximes of 2,3-benzocycloalkanones.The electronic absorption and NMR spectra of these molecules may be related to the degree of nonplanarity of the system resulting from polymethylene bridging.These molecules react with palladium bis(acetylacetonate) and its hexafluoro derivative to give soluble, monomeric cyclopalladated products.Rates of cyclopalladation were measured for these systems as well as for 2-(phenyl-d5)pyridine, and the results indicate the liklihood that for the less planar substrates the deprotonation step may show increasing importance over the electrophilic attack of palladium on the phenyl ring.The possible oxidative addition of palladium to a phenyl C-H bond cannot be ruled out.

Electrochemically enabled rhodium-catalyzed [4 + 2] annulations of arenes with alkynes

Herein, electrochemically driven, Rh(iii)-catalyzed regioselective annulations of arenes with alkynes have been established. The strategy, combining the use of a rhodium catalyst with electricity, not only avoids the need for using a stoichiometric amount of external oxidant, but also ensures that the transformations proceed under mild and green conditions, which enable broad functional group compatibility with a variety of substrates, including drugs and pharmaceutical motifs. Moreover, the electrolysis reaction was made operationally simple by employing an undivided cell, and proceeds efficiently in aqueous solution in air. This journal is

Acetic Acid-Promoted Rhodium(III)-Catalyzed Hydroarylation of Terminal Alkynes

Rhodium(III)-catalyzed hydroarylation of terminal alkynes has not previously been achieved because of the inevitable oligomerization and other side reactions. Here, we report a novel Cp?Rh(III)-catalyzed hydroarylation of terminal alkynes in acetic acid as solvent to facilitate the C-H bond activation and subsequent transformations. This reaction proceeds under mild conditions, providing an effective approach to the synthesis of alkenylated heterocycles in high to excellent yields (31-99%) with a broad substrate scope (37 examples) and good functional-group compatibility. In this transformation, the loading of the alkyne can be reduced to 1.2 equivalents, which indicates the significant role of HOAc in lowering the reaction temperature and suppressing the oligomerization of the terminal alkyne. Preliminary mechanistic studies are also presented.

Transition-Metal-Free Decarboxylative Arylation of 2-Picolinic Acids with Arenes under Air Conditions

A facile, transition-metal-free, and direct decarboxylative arylation of 2-picolinic acids with simple arenes is described. The oxidative decarboxylative arylation of 2-picolinic acids with arenes proceeds readily via N-chloro carbene intermediates to afford 2-arylpyridines in satisfactory to good yields under transition-metal-free conditions. This new type of decarboxylative arylation is operationally simple and scalable and exhibits high functional-group tolerance. Various synthetically useful functional groups, such as halogen atoms, methoxycarbonyl, and nitro, remain intact during the decarboxylative arylation of 2-picolinic acids.