32588-84-4

Upstream product

• 80504-86-5 1-(4-Methoxyphenyl)-1,3-nonadiene 
• 3761-92-0 n-hexylmagnesium bromide 
• 115878-50-7 1-chloro-3-(4-methoxyphenyl)propyl phenyl sulfoxide 
• 123-11-5 4-methoxy-benzaldehyde 
• 4282-40-0 1-Iodoheptane 
• 104-40-5 4-Nonylphenol 
• 74-88-4 methyl iodide 
• 3391-86-4 1-octen-3-ol 
• 140-67-0 Estragole 
• 738607-47-1 3-(4-methoxyphenyl)propyl phenyl sulfoxide 
• 111-25-1 1-bromo-hexane 
• 374754-93-5 (9-BBN)(CH₂)3(p-anisyl) 
• 7647-01-0 hydrogenchloride 
• 52754-68-4 1-(4-methoxy-phenyl)-nonan-1-one 

Downstream Products

• 104-40-5 4-Nonylphenol 

Relevant academic research and scientific papers

Nickel-Catalyzed C(sp3)-C(sp3) Cross-Electrophile Coupling of in Situ Generated NHP Esters with Unactivated Alkyl Bromides

The formation of C(sp3)-C(sp3) bonds by cross-coupling remains a challenge in synthesis. Here, we demonstrate a two-step, one-pot protocol for the in situ generation of N-hydroxyphthalimide esters and their nickel-catalyzed cross-electrophile coupling with unactivated alkyl bromides for the construction of 1°/1 ° C(sp3)-C(sp3) bonds. The conditions tolerate an array of functional groups, and mechanistic studies indicate that both substrates are converted to alkyl radicals during the reaction.

Suzuki-Miyaura cross-coupling of aryl and alkyl halides using palladium/imidazolium salt protocols

A simple new protocol for the high yielding Suzuki-Miyaura cross-couplings of aryl chlorides with aryl boronic acids using a palladium/imidazolium salt catalytic system is presented. The first examples of a palladium/imidazolium salt protocol for sp3-sp3 Suzuki-Miyaura couplings of alkyl halides are also disclosed.

Generation of magnesium carbenoids from 1-chloroalkyl phenyl sulfoxides with a Grignard reagent and applications to alkylation and olefin synthesis

Treatment of 1-chloroalkyl phenyl sulfoxides with a Grignard reagent at low temperature gave magnesium carbenoids in quantitative yields. The generated magnesium carbenoids were found to be stable at lower than -60°C for long periods of time and are reactive with Grignard reagents to give alkylated products. The reaction of the generated magnesium carbenoids with various kinds of lithium α-sulfonyl carbanions gave olefins with carbon-carbon bond-formation in good to high yields. This method offers a good way for the preparation of olefins. The scope and limitations of the above-mentioned reactions are described.

Mechanism of the Solution-Phase Reaction of Alkyl Sulfides Atomic Hydrogen. Reduction via a 9-S-3 Radical Intermediate

The low selectivity of benzyl alkyl sulfide fragmentation subsequent to its reaction with atomic hydrogen is indicative of a reaction that proceeds via an early transition state. The competitive reduction of a series of substituted-benzyl alkyl sulfides was insensitive to the substituent on the aromatic ring (ρ = -0.13, r = 0.99). The relative rates of fragmentation of a series of the substituted-benzyl alkyl sulfides gave a V-shaped Hammett plot. Both electron-donating and electron-withdrawing groups destabilized the transition state (ρ = +0.99, r = 0.999; ρ = -0.82, r = 0.992). Since the relative rates of disappearance of the alkyl benzyl sulfides are not substituent dependent, but the relative rates of fragmentation are, a 9-S-3 intermediate is preferred as the structure leading to products.

Novel extractants for the recovery of palladium

Novel ortho alkoxy substituted phenyl oxime compounds which are useful for selectively separating and recovering palladium from aqueous compositions and mixtures containing palladium and other metals.

METAL COMPLEXES IN ORGANIC SYNTHESIS. VIII. ALLYLIC ALCOHOLS AS STARTING MATERIALS IN PALLADIUM-CATALYZED WITTIG-TYPE OLEFINIZATIONS.

Allylic alcohols, aldehydes, and triphenylphosphine participate in a one-pot process catalyzed by palladium, which is formally equivalent to the Wittig olefinization. It can be applied to both aliphatic and aromatic aldehydes. The resulting olefins which appear as mixtures of stereoisomers were fully hydrogenated. Two different mechanisms can account for the observed results.

DOUBLE BOND FORMATION BY ONE POT PALLADIUM INDUCED REACTIONS BETWEEN ALDEHYDES, ALLYLIC ALCOHOLS AND TRIPHENYLPHOSPHINE

The reaction between several aldehydes, two allylic alcohols and triphenylphosphine under palladium catalysis leads to double bond formation, synthetically parallelizing the Wittig reaction.