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Upstream product

• 5720-05-8 4-methylphenylboronic acid 
• 69207-36-9 ethyl 6-methyl-4-phenylpyrimidin-2(1H)-one-5-carboxylate 
• 123237-03-6 ethyl 6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one-5-carboxylate 
• 1245716-47-5 ethyl 4-methyl-6-phenyl-2-(tosyloxy)pyrimidine-5-carboxylate 
• 69207-36-9 ethyl 2-hydroxy-4-methyl-6-phenylpyrimidine-5-carboxylate 
• 123043-88-9 5-ethoxycarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 106-38-7 para-bromotoluene 
• 17873-01-7 (4-methylphenyl)trimethoxysilane 

Relevant academic research and scientific papers

Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Bromides with Pyrimidin-2-yl Tosylates

A new protocol for the NiCl2-catalyzed cross-electrophile coupling of aryl bromides with pyrimidin-2-yl tosylates to give the corresponding C2-arylation pyrimidine derivatives has been developed. This study provides an improvement over previous methods by using pyrimidin-2-yl tosylates instead of halides as coupling partners that are stable and easily available.

Ni-catalyzed Suzuki-Miyaura coupling reactions of pyrimidin-2-yl phosphates, tosylates and pivalates with arylboronic acids

Ni-catalyzed Suzuki-Miyaura cross-coupling reactions of pyrimidin-2-yl phosphates, tosylates and pivalates with arylboronic acids were described. A wide array of functionalized pyrimidines have been prepared in impressive yields and show good tolerance to

Iron-catalyzed cross-coupling of heteroaromatic tosylates with alkyl and aryl Grignard reagents

An Fe(III)-catalyzed cross-coupling of N-heteroaromatic tosylates with aryl and alkyl Grignard reagents is presented. The reaction proceeds at -20°C to room temperature with short reaction time (15-30 min.), and the corresponding products are obtained with moderate to high yields. In particular, low-cost and abundantly available FeCl3 or Fe(acetylacetonate)3 catalyze the reaction without other special ligands. All tested N-heteroaromatic tosylates that are available including pyridine and pyrimidine derivatives were subject to the reaction, resulting in the expected products.

Palygorskite-anchored Pd complexes catalyze the coupling reactions of pyrimidin-2-yl sulfonates

In this work, an anchored Pd complex (PGS-APTES-Pd(OAc)2) was prepared via simple and green steps from the natural clay mineral palygorskite and was well characterized by XPS, XRD, IR, SEM, and EDX. This complex was further utilized as a fine catalyst for the C-C/C-N coupling reactions of pyrimidin-2-yl sulfonates. Subsequently, the cyclic utilization test indicated the high stability and sustainability of this PGS-APTES-Pd(OAc)2 catalyst, and no activation was required in the recycling process, providing an applicable and reusable catalyst in organic synthesis.

Palladium-Catalyzed Copper-Promoted Hiyama-Type Carbon-Carbon Cross-Coupling Reactions of Dihetaryl Disulfides as Electrophiles

Dihetaryl disulfides were used as electrophiles in a palladium-catalyzed carbon-carbon cross-coupling reaction with arylsilanes to realize a Hiyama-type reaction. This unique transformation shows high reactivity, excellent functional-group tolerance, and mild reaction conditions, making it an attractive alternative to conventional cross-coupling approaches for carbon-carbon bond construction.

Dehydrosulfurative arylation with concomitant oxidative dehydrogenation for rapid access to pyrimidine derivatives

This report describes a cascade reaction method for the synthesis of 2-arylpyrimidine derivatives via dehydrosulfurative carbon-carbon cross-coupling and concomitant oxidative dehydrogenation under a Pd/Cu catalytic system. It provides rapid and general access to a diverse range of 2-arylpyrimidines in a single step from a wide range of 3,4-dihydropyrimidin-1H-2-thiones (DHPMs) and arylboronic acids.

Wool-anchored Pd(OAc)2 complex: A highly active and reusable catalyst for desulfurative coupling reactions

A biomacromolecule-anchored palladium complex, wool-Pd(OAc)2, was prepared and characterized by IR, XPS, SEM and ICP. The new complex was used as a catalyst for the Liebeskind-Srogl desulfurative coupling reactions of pyrimidin-yl thioether derivatives with terminal alkynes and aryl boronic acids. Products were isolated in moderate to excellent yields. When 2-(phenylthio)-1,4-dihydropyrimidine derivatives were reacted with terminal alkynes and carboxyl acids, a domino reaction process was revealed. In these reactions, this novel and efficient catalyst was capable of being reused for at least nine rounds, with durable performance and wide substrate tolerance.

RETRACTED ARTICLE: Reusable biomacromolecule-Pd complex catalyzed C-C cross-coupling reactions via C-S cleavage of disulfides

A well-defined heterogeneous palladium catalyst, natural wool supported Pd(OAc)2-complex was found to be an effective catalyst for the C-S bonds cleavage and C-C bonds formation from 1,2-di(pyrimidin-2-yl)disulfane derivatives with arylboronic acids or terminal alkynes, giving the desired coupling products in moderate to excellent yields. The novel catalyst, which is stable and easy handling in experiment, was characterized by XPS, IR, SEM and ICP analysis. Subsequent analysis of the used catalyst after reaction revealed its negligible metal leaching and at least 10 rounds of recycled catalyzing capacity and wide range of substrate tolerance.

Chemo-controlled cross-coupling of Di(hetero)aryl disulfides with grignard reagents: C-C vs. C-S bond formation

A general protocol for the chemoselectivity-controlled C-C and C-S coupling reactions of di(hetero)aryl disulfides with Grignard reagents catalyzed by ferrocene and palladium acetate has been developed. Ferrocene favored the formation of C-S coupled products at low temperature, whereas C-C bond couplings were favored when palladium acetate was used. All the reactions proceeded with excellent chemoselectivity and in good yields under mild conditions, and a library of molecules with pyridine and pyrimidine scaffolds was produced.

Recyclable palladium catalyst on grapheme oxide for the C-C/C-N cross-coupling reactions of heteroaromatic sulfonates

Abstract A well-defined heterogeneous palladium catalyst, graphene oxide grafted with PdCl2, was prepared and found to be an effective catalyst for the C-C, C-N coupling of hetero aryl sulfonates with aryl boronic acids, terminal alkynes, amines, respectively, leading to the desired coupling products in moderate to excellent yields. The catalyst was characterized by XRD, IR, SEM, TEM, XPS and ICP. It is worthy noting that this catalyst offers a number of advantages such as high stability and negligible metal leaching. It also retains good activity for at least five successive runs without any additional activation treatment, showing a better performance than the well-known commercial Pd/C catalysts. This approach would be very useful from a practical viewpoint.