188527-65-3

Upstream product

• 4595-59-9 5-bromopyrimidine 
• 7029-31-4 bis(2-methylphenyl)zinc 
• 1722-12-9 2-chloropyrimidine 
• 932-31-0 ortho-tolylmagnesium bromide 
• 84109-17-1 2-methylphenylzinc chloride 
• 4595-60-2 2-bromopyrimidine 
• 16419-60-6 2-Methylphenylboronic acid 
• 7431-45-0 2-phenylpyrimidine 
• 3385-78-2 trimethyl indium 
• 544-97-8 dimethyl zinc(II) 
• 33872-80-9 o-tolyl magnesium chloride 

Downstream Products

• 1217887-49-4 C₁₂H₉F₃N₂ 
• 1246561-87-4 3-methyl-2-(pyrimidin-2-yl)phenyl acetate 
• 1383625-75-9 2-(2-methyl-6-triethylsilylphenyl)pyrimidine 
• 1383625-74-8 methyl 2-{2-(pyrimidin-2-yl)-3-triethylsilylphenyl}acetate 
• 1421623-24-6 2-(2-methyl-6-((triisopropylsilyl)ethynyl)phenyl)pyrimidine 
• 1436430-75-9 ethyl 2-(3-methyl-2-(pyrimidin-2-yl)phenyl)acetate 

Relevant academic research and scientific papers

Efficient Negishi coupling reactions of aryl chlorides catalyzed by binuclear and mononuclear nickel-N-heterocyclic carbene complexes

(Chemical Equation Presented) We describe the first nickel-N-heterocyclic carbene catalyzed Negishi cross-coupling reaction of a variety of unactivated aryl chlorides, heterocyclic chlorides, aryl dichlorides, and vinyl chloride. The mononuclear and binuclear nickel-NHC complexes supported by heteroarene-functionalized NHC ligands are found to be highly efficient for the coupling of unactivated aryl chlorides and organozinc reagents, leading to biaryls and terphenyls in good to excellent yields under mild conditions. For all aryl chlorides, the binuclear nickel catalysts show activities higher than those of mononuclear nickel complexes because of possible bimetallic cooperative effect.

Palladium-Catalyzed Electrochemical C-H Alkylation of Arenes

Palladium-catalyzed electrochemical C-H functionalization reactions have emerged as attractive tools for organic synthesis. This process offers an alternative to conventional methods that require harsh chemical oxidants. However, this electrolysis requires divided cells to avoid catalyst deactivation by cathodic reduction. Herein, we report the first example of palladium-catalyzed electrochemical C-H alkylation of arenes using undivided electrochemical cells in water, thereby providing a practical solution for the introduction of alkyl groups into arenes.

Triorganoindium reagents in Rh-catalyzed C–H activation/C–C cross-coupling reactions of 2-arylpyridines

The activation of C–H bonds through catalytic reactions using transition metals is an important challenge in organic chemistry in which the intermediates are related to those produced in the classical cross-coupling reactions. As part of our research program devoted to the development of metal-catalyzed reactions using indium organometallics, a protocol for the C–H activation and C–C coupling of 2-arylpyridines with triorganoindium reagents under Rh(I) catalysis is reported. Under the optimized conditions, we found that Me3In and Ar3In reagents reacted with 2-arylpyridines and related compounds in the presence of Rh(PPh3)3Cl, in PhCl/THF (9:1), at 120?C for 48 h, to afford the ortho-coupling products in moderate to good yields. The nitrogen atom in the pyridine ring acts as a directing group to assist the functionalization at the ortho position of the aryl group forming a new C–C bond at this position.

Nickel-catalyzed N-heterocycle-directed cross-coupling of fluorinated arenes with organozinc reagents

Nickel-catalyzed N-heteroaromatics, such as pyridine, pyrazine or pyrimidine-directed cross-coupling of fluorinated arenes with organozinc reagents in the presence of sodium and PCy3 was reported.

Synthesis, characterization, and catalytic activity of nickel(II) alkyl complexes supported by pyrrole-diphosphine ligands

The organometallic Ni(II) chemistry of the pyrrole-based pincer ligands (P2RPyr)- (P2RPyr = 2,5-(R2PCH2)2C4H2N, R = Ph, Cy) is reported. Reactions of Grignard reagents with [NiCl(P 2RPyr)] afford a variety of alkyl and aryl complexes (methyl, ethyl, benzyl, phenyl, and allyl) that all display square-planar geometries about nickel. The hydride complex [NiH(P2 CyPyr)] can also prepared either through treatment of [NiCl(P 2CyPyr)] with LiHBEt3 or by reaction of H(P2RPyr) with [Ni(COD)2] (COD = 1,4-cyclooctadiene). Reactions of the methyl and hydride complexes with CO and CO2, respectively, evince clean migratory insertion chemistry of the Ni-C and Ni-H bonds. Both the alkyl and chloride complexes are active catalysts for the Kumada coupling of aryl chlorides and aryl or alkyl Grignard reagents at room temperature. The solid-state structures of several of the complexes are reported.

Sequential protocol for C(sp3)-H carboxylation with CO 2: Transition-metal-catalyzed benzylic C-H silylation and fluoride-mediated carboxylation

One of the most challenging transformations in current organic chemistry is the catalytic carboxylation of a C(sp3)-H bond using CO2 gas, an inexpensive and ubiquitous C1 source. A sequential protocol for C(sp3)-H carboxylation by employing a nitrogen-directed, metal-assisted, C-H activation/catalytic silylation reaction in conjunction with fluoride-mediated carboxylation with CO2 was established. The carboxylation proceeded only at the benzylic C(sp3)-Si bond, not at the aromatic C(sp2)-Si, which is advantageous for further manipulations of the products.

[Pd(Cl)2(P(NC5H10)(C6H 11)2)2] - A highly effective and extremely versatile palladium-based negishi catalyst that efficiently and reliably operates at low catalyst loadings

[Pd(Cl)2(P(NC5H10)-(C6H 11)2]2] (1) has been prepared in quantitative yield by reacting commercially available [Pd(cod)(Cl)2] (cod = cyclooctadiene) with readily prepared 1-(dicyclohexylphosphanyl)piperidine in toluene under N2 within a few minutes at room temperature. Complex 1 has proved to be an excellent Negishi catalyst, capable of quantitatively coupling a wide variety of electronically activated, non-activated, deactivated, sterically hindered, heterocyclic, and functionalized aryl bromides with various (also heterocyclic) arylzinc reagents, typically within a few minutes at 100°C in the presence of just 0.01 mol% of catalyst. Aryl bromides containing nitro, nitrile, ether, ester, hydroxy, carbonyl, and carboxyl groups, as well as acetais, lactones, amides, anilines, alkenes, carboxylic acids, acetic acids, and pyridines and pyrimidines, have been successfully used as coupling partners. Furthermore, electronic and steric variations are tolerated in both reaction partners. Experimental observations strongly indicate that a molecular mechanism is operative.

Palladium-Catalyzed Regioselective C-H Bond ortho-Acetoxylation of Arylpyrimidines

An efficient and regioselective palladium-catalyzed ortho C-H acetoxylation reaction was developed to afford, ortho monoacetoxylated arylpyrimidmes in good to excellent yields by using cupric trifluoroacetate as a cocatalyst. A wide variety of oxygenated

Palladium-catalyzed monoselective halogenation of C-H bonds: Efficient access to halogenated arylpyrimidines using calcium halides

A wide variety of ortho-halogenated arylpyrimidines were prepared with high monoselectivity and functional-group tolerance by using calcium halides as crucial halogenating agents and cupric trifluoroacetate as oxidant in the presence of air.

Pd(II)-Catalyzed ortho-trifluoromethylation of arenes using TFA as a promoter

"Chemical equation presented" A Pd(II)-catalyzed C-H activation/trifluoromethylation of arenes with an electrophilic trifluoromethylation reagent using diverse heterocycle directing groups is reported. The presence of trifluoroacetic acid is crucial for this catalytic reaction.