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Upstream product

• 696-62-8 para-iodoanisole 
• 693-02-7 hex-1-yne 
• 3179-10-0 (E)-1-methoxy-4-(2-nitrovinyl)benzene 
• 693-04-9 butyl magnesium bromide 
• 88626-90-8 BuMnCl 
• 42599-18-8 (E)-1-hexenyldihydroxyborane 
• 624-20-4 1,2-dibromohexane 
• 5720-07-0 4-methoxyphenylboronic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 124582-25-8 (E)-tributyl(hex-1-en-1-yl)stannane 
• 592-41-6 1-hexene 
• 623-12-1 4-chloromethoxybenzene 
• 21406-61-1 pentyltriphenylphosphonium bromide 
• 105-13-5 4-Methoxybenzyl alcohol 

Relevant academic research and scientific papers

An amphiphilic resin-supported palladium catalyst for high-throughput cross-coupling in water

(figure presented) The Suzuki-Miyaura coupling of aryl halides (8 varieties) and aryl-or vinylboronic acids (12 varieties) took place in water in the presence of a palladium complex of an amphiphilic polystyrene-poly(ethylene glycol) copolymer resin-supported N-anchored 2-aza-1,3-bis(diphenylphosphino)-propane ligand and potassium carbonate to give uniform and quantitative yields of the corresponding biaryls (96 varieties).

Iron-catalyzed coupling reaction between 1,1-dichloro-1-alkenes and Grignard reagents

This letter reports the coupling reaction of Grignard reagents with 1,1-dichloro-1-alkenes in the presence of the environmentally friendly iron(III) catalyst. This non-toxic procedure is general and provides the di-coupled products as the major compounds. The scope and limitations of this new reaction are described.

1-Methyl-1H-tetrazol-5-yl (MT) sulfones in the Julia-Kocienski olefination: Comparison with the PT and the TBT sulfones

The stability and the stereoselectivity of newly prepared n-pentyl 1-methyl-1H-tetrazol-5-yl (MT) sulfone 1a in the Julia-Kocienski reactions were compared with those of the PT sulfone 1b and the TBT sulfone 1c. The improved stability of the anion derived from the n-pentyl MT sulfone 1a enhanced the efficiency of the olefination reactions and gave higher yields of the product alkenes 3 compared with the PT sulfone 1b. Especially high E-selectivity and high yields were obtained from the reaction with aromatic aldehydes and α,β-unsaturated aldehydes. The selectivity of 1a was not so sensitive to the change of base counter ion compared with the PT sulfone 1b. The reaction of the MT sulfones having either ethyl or a longer alkyl chain also gave E-alkenes selectively in high yields.

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.

Metal-Catalyzed Remote Functionalization of ω-Ene Unsaturated Ethers: Towards Functionalized Vinyl Species

The combined ruthenium-catalyzed chain walking with the nickel-catalyzed cross-coupling reaction of ω-alkenyl ethers provide a unique entry to functionalized vinyl species. This transformation illustrates the power and flexibility of remote functionalization by demonstrating the compatibility of two independent reactions involving unrelated sites.

A highly efficient and recyclable Pd(PPh3)4/PEG-400 system for Stille cross-coupling reactions of organostannanes with aryl bromides

Pd(PPh3)4 in PEG-400 is shown to be a highly efficient catalyst for the Stille cross-coupling reactions of various organotin compounds with aryl bromides. The reaction could be conducted at 80 °C using NaOAc as base, yielding a variety of biaryls, alkynes and alkenes in good to excellent yields. The isolation of the products was readily performed by extraction with petroleum ether and the Pd(PPh3)4/PEG-400 system could be easily recycled and reused five times without any significant loss of activity.

Active Ruthenium (0) Nanoparticles Catalyzed Wittig-Type Olefination Reaction

Abstract: Five different Ru metal precursors were reduced in imidazolium based ionic liquids under hydrogen atmosphere (4?bar) at 50 °C to obtain well-dispersed and stable Ru nanoparticles. Transmission electron microscopy (TEM) analysis confirmed size of well dispersed ionic liquid mediated Ru particles (Ru NPs) of 5?nm (±0.5) in diameter. These ruthenium nanoparticles (in ionic liquids) were used for Wittig type olefination reaction under mild reaction environment (70 °C and 1?h). The corresponding stilbenes were obtained in good yield with low-average selectivity. The proposed methodology is especially efficient for the synthesis of stilbenes as they were synthesized in the absence of any additive (as a hydrogen acceptor). The new catalytic system was also successfully applied for the synthesis of polymethoxylated and polyhydroxylated stilbenes, including resveratrol and DMU-212. Graphical Abstract: [Figure not available: see fulltext.]

The aromatic production of olefins

PROBLEM TO BE SOLVED: To provide a method for efficiently producing aromatic olefins useful for various functional chemicals.SOLUTION: Aromatic olefins are produced by reaction of an aromatic compound with an epoxide or aldehyde in the presence of a solid

E- and Z-Selective Transfer Semihydrogenation of Alkynes Catalyzed by Standard Ruthenium Olefin Metathesis Catalysts

Selective transfer semihydrogenation of alkynes to yield alkenes was achieved with commercial first and second generation Hoveyda-Grubbs catalysts and formic acid as a hydrogen donor. This catalytic system is distinguished by its selectivity and compatibility with many functional groups (halogens, cyano, nitro, sulfide, alkenes). The metathetic activity of the ruthenium catalysts may be utilized in tandem sequences of olefin metathesis plus alkyne reduction.

SINGLE-STEP PROCESS FOR THE PREPARATION OF ARYL OLEFINS

The present invention relates to the single-step process for the synthesis of aryl olefin compounds of Formula (1) by reacting aryl aldehydes with alkyl aldehydes in presence of malononitrile and acid or base or salt, optionally in presence of solvent.