79958-53-5

Upstream product

• 917-64-6 methyl magnesium iodide 
• 142039-24-5 2-[(E)-2-(4-Methoxy-phenyl)-vinyl]-2-methyl-[1,3]dithiolane 
• 3179-10-0 (E)-1-methoxy-4-(2-nitrovinyl)benzene 
• 558-17-8 tert-Butyl iodide 
• 696-62-8 para-iodoanisole 
• 86595-37-1 trans-2-tert-butylvinylboronic acid 
• 630-19-3 pivalaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 93296-09-4 4-methoxyphenylzinc chloride 
• 558-37-2 tert-butylethylene 
• 75-89-8 2,2,2-trifluoroethanol 
• 623-12-1 4-chloromethoxybenzene 
• 270921-39-6 (4-methoxyphenyl)methyl methyl carbonate 
• 17105-65-6 dimethyl 4-methoxybenzylphosphonate 

Downstream Products

• 65853-51-2 3,3-dimethyl-1-(4-methoxyphenyl)butan-2-one 
• 85157-92-2 1-(4-methoxyphenyl)-3,3-dimethylbutan-1-one 
• 79958-52-4 1-[(1Z)-3,3-dimethylbut-1-en-1-yl]-4-methoxybenzene 

Relevant academic research and scientific papers

Cu-mediated or metal-free alkylation of gem-dibromoalkenes with tertiary, secondary and primary alkyl Grignard reagents

A novel copper-mediated or transition-metal-free alkylation of gem-dibromoalkenes with tertiary, secondary and primary alkyl Grignard reagents was described. The outcomes of these reactions were found to be highly dependent on the reaction conditions and

Photoinduced copper-catalyzed dual decarboxylative coupling of α,β-unsaturated carboxylic acids with redox-active esters

The first photoinduced copper-catalyzed dual decarboxylative cross-coupling of α,β-unsaturated carboxylic acids and redox-active esters has been developed. This reaction enabled C(sp2)–C(sp3) bond formation, which afforded a variety of synthetically valuable alkene derivatives. Many α,β-unsaturated carboxylic acids and redox-active ester derivatives were tolerant to this reaction. The reaction also tolerated many common functional groups.

RETRACTED ARTICLE: Copper-Catalyzed Decarboxylative C(sp2)-C(sp3) and C(sp)-C(sp3) Coupling of Substituted Cinnamic Acids and 3-Phenyl Propiolic Acid with N-Tosyl Oxaziridines

A mild and efficient strategy for decarboxylative C(sp2)-C(sp3) and C(sp)-C(sp3) coupling of α,β-unsaturated carboxylic acids such as substituted cinnamic acids and 3-phenyl propiolic acid with N-Tosyl oxaziridines was developed. The corresponding products were achieved in moderate to good yields with excellent stereoselectivity. Base-free and oxidant-free conditions allow good functional group tolerance. Radical inhibitors such as TEMPO and BHT completely suppressed the reactions suggesting a radical mechanism was involved. This study is supposed to broaden the frontier of oxaziridines' chemistry and to open up a novel cascade for alkylating reagents.

Dual nickel- and photoredox-catalyzed reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides

A novel reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides has been realized via photoredox/nickel dual catalysis to produce vinyl arene derivatives bearing all-carbon quaternary centers with excellent E-selectivity. A stoichiometric metal reductant could be avoided by employing commercially available N,N,N′,N′-tetramethylethylenediamine (TMEDA) as the terminal reductant.

A Highly Reduced Ni-Li-Olefin Complex for Catalytic Kumada-Corriu Cross-Couplings

The catalytic activity of a highly reduced Ni catalyst in the context of a Kumada-Corriu cross-coupling has been studied. This nickel complex is characterized by its high electron density, stabilized by simple olefin ligands in combination with two Li ions. Landmark reactivity has been found with this precatalyst which operates at cryogenic temperatures, thus allowing the presence of sensitive functionalities. Structural elucidation of oxidative addition intermediates and their reactivity suggest highly reduced species being operative in the C-C bond forming event.

Diastereodivergent Reductive Cross Coupling of Alkynes through Tandem Catalysis: Z- and E-Selective Hydroarylation of Terminal Alkynes

A diastereodivergent hydroarylation of terminal alkynes is accomplished using tandem catalysis. The hydroarylation allows highly selective synthesis of both E and Z diastereoisomers of aryl alkenes, from the same set of starting materials, using the same combination of palladium and copper catalysts. The selectivity is controlled by simple changes in the stoichiometry of the alcohol additive. The hydroarylation has excellent substrate scope and can be accomplished in the presence of various classes of compounds, including esters, nitriles, alkyl halides, epoxides, carbamates, acetals, ethers, silyl ethers, and thioethers. The Z-selective hydroarylation is accomplished using a new approach based on tandem Sonogashira coupling and catalytic semireduction. The E-selective hydroarylation involves an additional catalytic isomerization of the Z-alkene. Our explorations of the reaction mechanism explain the role of individual reaction components and how the subtle changes in the reaction conditions influence the rates of specific steps of the hydroarylation. Our studies also show that, although the Z- and E-selective hydroarylation reactions are mechanistically closely related, the roles of the palladium and copper catalysts in the two reactions are different.

Copper- and Nickel-Catalyzed Cross-Coupling Reaction of Monofluoroalkenes with Tertiary, Secondary, and Primary Alkyl and Aryl Grignard Reagents

A highly efficient cross-coupling reaction of monofluoroalkenes with tertiary, secondary, and primary alkyl and aryl Grignard reagents in the presence of a catalytic amount of copper or nickel catalyst, respectively, has been developed. The reactions proceeded smoothly at room temperature, providing (E)-alkene isomers in moderate to high yields. Plausible mechanisms of the Ni-catalyzed coupling reaction of monofluoroalkene with Grignard reagents are suggested.

Irradiation-Induced Heck Reaction of Unactivated Alkyl Halides at Room Temperature

The palladium-catalyzed Mizoroki-Heck reaction is arguably one of the most significant carbon-carbon bond-construction reactions to be discovered in the last 50 years, with a tremendous number of applications in the production of chemicals. This Nobel-Prize-winning transformation has yet to overcome the obstacle of its general application in a range of alkyl electrophiles, especially tertiary alkyl halides that possess eliminable β-hydrogen atoms. Whereas most palladium-catalyzed cross-coupling reactions utilize the ground-state reactivity of palladium complexes under thermal conditions and generally apply a single ligand system, we report that the palladium-catalyzed Heck reaction proceeds smoothly at room temperature with a variety of tertiary, secondary, and primary alkyl bromides upon irradiation with blue light-emitting diodes in the presence of a dual phosphine ligand system. We rationalize that this unprecedented transformation is achieved by utilizing the photoexcited-state reactivity of the palladium complex to enhance oxidative addition and suppress undesired β-hydride elimination.

Palladium-catalyzed benzylic substitution of benzyl carbonates with phosphorus nucleophiles

A wide range of benzyl carbonates reacted with dimethyl phosphonate or diphenylphosphine oxide in the presence of the palladium catalyst, [Pd(η3-allyl)Cl]2DPEphos, to give dimethyl benzylphosphonates and benzyldiphenylphosphine oxides in high yields. The catalytic phosphonylation was applied to the one-pot synthesis of alkenes from the benzyl esters.