84591-12-8

Upstream product

• 14774-77-7 p-methoxyphenyllithium 
• 31600-88-1 m-methoxyphenyllithium 
• 1711-05-3 m-anisoyl chloride 
• 70744-47-7 (p-methoxyphenyl)tri-n-butylstannane 
• 696-62-8 para-iodoanisole 
• 100-66-3 methoxybenzene 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 

Downstream Products

• 18855-13-5 Biphenyl-3,4'-diol 
• 1439362-32-9 C₅₆H₆₂O₆ 
• 1439362-33-0 C₅₈H₆₆O₆ 
• 1439362-34-1 C₆₀H₇₀O₆ 
• 1439362-35-2 C₆₂H₇₄O₆ 
• 1439362-36-3 C₆₄H₇₈O₆ 
• 1439362-37-4 C₆₆H₈₂O₆ 
• 1439362-38-5 C₆₈H₈₆O₆ 

Relevant academic research and scientific papers

Copper catalysed Gomberg-Bachmann-Hey reactions of arenediazonium tetrafluoroborates and heteroarenediazonium o-benzenedisulfonimides. Synthetic and mechanistic aspects

Gomberg-Bachmann-Hey reactions were carried out in the presence of copper as a catalyst and gave rise to biaryls or heterobiaryls in good yields and in mild reaction conditions. A computational study of some key points of the reaction was performed. The results are coherent with the experimental data and confirm some aspects of the mechanism. The reaction free energies for the reduction in benzene by CuI of a set of 40 (hetero)arenediazonium tetrafluoroborates were calculated. Both the experiments and the calculations showed that in the coupling with substituted solvents (toluene, bromobenzene, nitrobenzene and anisole) the binding to the ortho position was always favoured.

Palladium-catalyzed cross-coupling of aroyl chlorides with aryl stannanes in the presence of triethylsilane: Efficient access to aromatic ketones

Herein, we report the development of a palladium-catalyzed cross-coupling reaction that focuses on the preparation of aromatic ketones. Aroyl chlorides react quickly at 120 °C with aryl stannanes in the presence of Pd(PPh3)4 and Et3SiH to efficiently give the corresponding ketones without the formation of significant decarbonylated byproducts. In other words, the decarbonylative side reaction is practically suppressed by simply adding Et3SiH to the reaction mixture, which reduces the amount of biaryl impurities in the products.

Urea-based organocatalyst catalyzed direct C–H bond arylations of unactivated arenes

A simple 1,3-diethylurea was demonstrated to catalyze transition-metal-free arylations of unactivated aromatic C–H bonds with aryl iodides in the presence of t-BuOK. A broad range of aryl iodides with different arenes could couple in moderate to excellent yields. The mechanistic experiment results indicated that the radical is involved in this transformation.

A Foldamer-Based Organocatalyst for Direct Arylations of Unactivated Arenes

It was demonstrated that a simple yet well-folded pyridone dimer, possessing two convergently aligned electron-rich O atoms for potassium binding, can serve as a highly efficient organocatalyst for catalyzing transition-metal-free arylations of unactivated aromatic C-H bonds with aryl halides in the presence of t-BuOK. A wide range of aryl iodides could be cross-coupled with unactivated arenes in moderate to excellent yields. The experiments using radical-scavenging reagents confirm the participation of radicals in this catalytic transformation.

Rhodium Complexes of 2,6-Bis(dialkylphosphinomethyl)pyridines: Improved C-H Activation, Expanded Reaction Scope, and Catalytic Direct Arylation

The reactivity of (PNP)Rh(Ph) (PNP = 2,6-bis(dialkylphosphinomethyl)pyridine) toward a variety of electrophiles (Ar-I, ArCH2Cl, O2, I2, B2pin2, and ArSO3H) was explored, and several new modes of oxidative reactivity were observed. Substituting tBu2P for iPr2P provided 100-fold rate enhancement toward C-H bond activation and addressed the previously reported challenge of N2 inhibition. Studying the stoichiometric reactivity of (PNP)Rh complexes toward C-H cleavage and oxidative functionalization led to (PNP)Rh-catalyzed cross-coupling of aryl iodides with sp2 and sp3 C-H bonds.

A macrocyclic aromatic pyridone pentamer as a highly efficient organocatalyst for the direct arylations of unactivated arenes

A macrocyclic aromatic pyridone pentamer was shown to catalyze highly efficient transition-metal-free arylations of unactivated aromatic C-H bonds with aryl iodides and bromides in the presence of potassium tert-butoxide. The Royal Society of Chemistry.

Transition-metal-free highly chemo- and regioselective arylation of unactivated arenes with aryl halides over recyclable heterogeneous catalysts

A novel heterogeneous catalysis system using metal-organic frameworks as catalyst demonstrated excellent chemo- and regioselectivity for the direct arylation of unactivated arenes with aryl iodides/bromides without the assistance of any transition metals.

Direct arylation of unactivated aromatic C-H bonds catalyzed by a stable organic radical

A stable zwitterionic radical can catalyze direct arylation of unactivated aromatic C-H bonds via a chain homolytic aromatic substitution mechanism in the presence of potassium tert-butoxide.

An efficient organocatalytic method for constructing biaryls through aromatic C-H activation

The direct functionalization of C-H bonds has drawn the attention of chemists for almost a century. C-H activation has mainly been achieved through four metal-mediated pathways: oxidative addition, electrophilic substitution, σ-bond metathesis and metal-associated carbene/nitrene/oxo insertion. However, the identification of methods that do not require transition-metal catalysts is important because methods involving such catalysts are often expensive. Another advantage would be that the requirement to remove metallic impurities from products could be avoided, an important issue in the synthesis of pharmaceutical compounds. Here, we describe the identification of a cross-coupling between aryl iodides/bromides and the C-H bonds of arenes that is mediated solely by the presence of 1,10-phenanthroline as catalyst in the presence of KOt-Bu as a base. This apparently transition-metal-free process provides a new strategy with which to achieve direct C-H functionalization.

An investigation of the reduction in aqueous acetonitrile of 4-methoxybenzenediazonium ion by the tetrakis(acetonitrile)Cu(i) cation catalysed by hydrogenphosphate dianion

In aqueous acetonitrile containing a phosphate buffer, 4- methoxybenzenediazonium ion is reduced by one or more of the partially aquated cations derived from tetrakis(acetonitrile)Cu(i) cation in this medium. Investigation of the reaction mechanism indicates the rate determining step to be the association of the diazonium ion with the hydrogenphosphate dianion to give an adduct which then undergoes reduction by Cu(i). The reaction gives a range of products which have been identified and quantified by GC. One of these, 4-methoxyphenol was unexpected in the reducing conditions; its presence could be explained by the disproportionation of a 4-methoxyphenylcopper(ii) complex giving bis(4-methoxyphenyl)copper(iii) which reacts with water to produce the phenol and an equivalent amount of methoxybenzene. A scheme is proposed which accounts for all the observed products and computer modelling gives a satisfactory description of the distributions of the five major products as functions of the relative proportions of the reactants for dilute conditions and those where the reductant is in excess. When the diazonium ion is in excess, the behaviour of the model and the experimental reactant accountability suggest the occurrence of additional reactions which give products unobserved by GC. This journal is The Royal Society of Chemistry.