79958-52-4

Upstream product

• 677-22-5 tert-butylmagnesium chloride 
• 768-60-5 4-methoxyphenylacetylen 
• 558-17-8 tert-Butyl iodide 
• 630-19-3 pivalaldehyde 
• 637-69-4 4-Methoxystyrene 
• 75-98-9 Trimethylacetic acid 
• 79958-53-5 (E)-1-(3,3-dimethylbut-1-en-1-yl)-4-methoxybenzene 
• 66582-09-0 1-(3,3-dimethylbut-1-yn-1-yl)-4-methoxybenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 507-19-7 t-butyl bromide 
• 6303-59-9 (E)-4-(2-bromo-vinyl)-anisole 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 60512-57-4 1-(2,2-dibromovinyl)-4-methoxybenzene 

Downstream Products

• 79958-53-5 (E)-1-(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

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.

Cis-Selective Decarboxylative Alkenylation of Aliphatic Carboxylic Acids with Vinyl Arenes Enabled by Photoredox/Palladium/Uphill Triple Catalysis

An iridium photoredox catalyst in combination with phenanthroline-supported palladium catalyst catalyzes decarboxylative alkenylation of tertiary and secondary aliphatic carboxylic acids with vinyl arenes to deliver β-alkylated styrenes with Z-selectivity. A broad scope of aliphatic carboxylic acids, including amino acids, exhibit as amenable substrates, and external oxidant is not required. The reaction proceeds by synergistic utilization of both energy-transfer and electron-transfer reactivity of iridium photoredox catalyst merging with palladium-catalyzed hydride elimination and insertion.

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.

Metal-Free Oxidative Decarbonylative Hydroalkylation of Alkynes with Secondary and Tertiary Alkyl Aldehydes

A new, metal-free, radical-mediated oxidative decarbonylative hydroalkylation of various alkynes with secondary and tertiary alkyl aldehydes using di-tert-butyl peroxide (DTBP) as oxidant is presented. This method enables the simultaneous formation of a C C bond and a C H bond through a sequence of decarbonylation, radical addition and protonation, and provides a straightforward route for transforming alkynes into alkenes with high compatibility with both alkynes and alkyl aldehydes. (Figure presented.) .

Silver-catalyzed regioselective carbomagnesiation of alkynes with alkyl halides and Grignard reagents

A silver-catalyzed carbomagnesiation of alkynes with alkyl halides and Grignard reagents afforded alkenyl Grignard reagents regioselectively, where the alkyl group of the alkyl halide, but not that of the Grignard reagent, was introduced into the alkyne.

Silver-catalyzed carbomagnesiation of terminal aryl and silyl alkynes and enynes in the presence of 1,2-dibromoethane

Regioselective carbomagnesiation of terminal alkynes and enynes with alkyl Grignard reagents has been achieved by the combined use of a silver catalyst and 1,2-dibromoethane. The Royal Society of Chemistry 2009.

Acid Catalysis induces a Total Change from Retention to Inversion of Configuration in CO2 Elimination from β-Lactones

With increasing acidity of the reaction medium the stereochemistry of the CO2 elimination from cis-3-t-butyl-4-(p-methoxyphenyl)oxetan-2-one (1a) and from cis-3-t-butyl-4-pheyloxetan-2-one (1b) gradually changes from total retention to total inversion of configuration, so that sterically pure (Z)- and (E)-3,3-dimethyl-1-(p-methoxyphenyl)but-1-ene (3a) and (7a) and (Z)- and (E)-3,3-dimethyl-1-phenylbut-1-ene (3b) and (7b) may be obtained from (1a) and (1b), respectively.