31169-38-7

Upstream product

• 96-40-2 2-cyclopenten-1-yl chloride 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 64-19-7 acetic acid 
• 696-62-8 para-iodoanisole 
• 142-29-0 cyclopentene 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 20657-21-0 3-acetoxycyclopent-1-ene 
• 100-66-3 methoxybenzene 
• 64740-90-5 1-cyclopenten-1-yl phenyl sulfone 
• 103594-89-4 4-methoxyphenyltitanium triisopropoxide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 131161-69-8 (E)-1-(2-cyclopropylvinyl)-4-methoxybenzene 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 109698-43-3 1-<4'-Methoxy-phenyl>-4.5.6.7.10.10-hexachlor-4.7-methylen-2.3.4.7.8.9-hexahydro-inden 

Relevant academic research and scientific papers

Cu-Catalyzed Oxidative Allylic C-H Arylation of Inexpensive Alkenes with (Hetero)Aryl Boronic Acids

Herein, we present a regioselective Cu-catalyzed oxidative allylic C(sp3)-H arylation by radical relay using a broad range of heteroaryl boronic acids with inexpensive and readily available unactivated terminal and internal olefins. This C(sp2)-C(sp3) allyl coupling has the advantage of using cheap, abundant, and nontoxic Cu2O without the need to use prefunctionalized alkenes, thus offering an alternative method to allylic arylation reactions that employ more traditional coupling partners with preinstalled leaving groups (LGs) at the allylic position.

Controlling olefin isomerization in the heck reaction with neopentyl phosphine ligands

The use of neopentyl phosphine ligands was examined in the coupling of aryl bromides with alkenes. Di-tert-butylneopentylphosphine (DTBNpP) was found to promote Heck couplings with aryl bromides at ambient temperature. In the Heck coupling of cyclic alkenes, the degree of alkene isomerization was found to be controlled by the choice of ligand with DTBNpP promoting isomerization to a much greater extent than trineopentylphosphine (TNpP). Under optimal conditions, DTBNpP provides high selectivity for 2-aryl-2,3-dihydrofuran in the arylation of 2,3-dihydrofuran, whereas TNpP provided high selectivity for the isomeric 2-aryl-2,5-dihydrofuran. A similar complementary product selectivity is seen in the Heck coupling of cyclopentene. Heck coupling of 2-bromophenols or 2-bromoanilides with 2,3-dihydrofurans affords 2,5-epoxybenzoxepin and 2,5-epoxybenzazepins, respectively.

A method for the net contra-thermodynamic isomerization of cyclic trisubstituted alkenes

A simple sequence for the net contra-thermodynamic isomerization of cyclic trisubstituted alkenes is reported consisting of a radical addition of p-chlorothiophenol, followed by oxidation to the sulfoxide and thermal syn-elimination to give the least substituted isomeric cycloalkene.

Mechanism of the Ni(0)-catalyzed vinylcyclopropane-cyclopentene rearrangement

(Chemical Equation Presented) A combination of physical organic experiments and quantum chemical calculations were used to construct a detailed mechanistic model for the Ni(0)-N-heterocyclic carbene-catalyzed vinylcyclopropane- cyclopentene rearrangement

Heck reaction of aryl halides with linear or cyclic alkenes catalysed by a tetraphosphine/palladium catalyst

cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C 3H5)]2 system catalyses efficiently the Heck reaction of aryl halides with linear alkenes such as pent-1-ene, oct-1-ene or dec-1-ene. Selectivities up to 70% in favour of E-1-arylalk-1-ene isomers can be obtained. In the presence of cyclic alkenes the selectivities of the reactions strongly depends on the ring size. Addition to cyclohexene or cycloheptene led mainly to 1-arylcycloalk-3-ene derivatives. On the other hand, addition to cyclooctene led to 1-arylcycloalk-1-ene adducts.

A new cine-substitution of alkenyl sulfones with aryltitanium reagents catalyzed by rhodium: Mechanistic studies and catalytic asymmetric synthesis of allylarenes

The reaction of alkenyl sulfones with aryltitanium triisopropoxide (ArTi(OPr-i )3) in the presence of 3 mol % of [Rh(OH)((S)-binap)]2 in THF at 40 °C gave high yield of cine-substitution products. The catalytic cycle was established by deuterium-labeling studies, and it was applied to catalytic asymmetric synthesis of allylarenes which proceeds with over 99% enantioselectivity. Copyright

Highly selective palladium-catalyzed Heck reactions of aryl bromides with cycloalkenes

Formula presented The influence of palladium catalysts and reaction conditions on the selectivity of Heck reactions of aryl bromides with cyclohexene and cyclopentene has been investigated. It is shown that the addition of DMSO as a cosolvent leads to improved selectivities of nonconjugated aryl olefins. On the other hand, high selectivities for conjugated arylcyclopentenes have been obtained with the catalytic system DMA/Na2-CO3/Pd2(dba) 3·dba/PCy3.

Molybdenum(II)-catalyzed allylation of electron-rich aromatics and heteroaromatics

The stable, readily available molybdenum(II) complexes [Mo(CO)4Br2]2 (B) and Mo(CO)3(MeCN)2-(SnCl3)Cl (C) have been found to catalyze C-C bond- forming allylic substitution with electronrich aromatics (e.g., 15 + PhOMe → 62) and heteroaromatics (e.g., 15 + 36 → 88) as nucleophiles under mild conditions (room temperature, 30 min-3 h). Remarkable is the para-selectivity for anisole, whereas phenol tends to favor ortho-substitution in certain instances. Mechanistic and stereochemical experiments are indicative of Lewis-acid catalysis rather than a metal template-controlled process.

Molybdenum(II)-catalyzed alkylation of electron-rich aromatics with allylic acetates

The molybdenum(II) complex [Mo(CO)4Br2]2 has been found to catalyze allylic substitution with aromatic ethers, e.g., anisole (7), as nucleophiles. The reaction is remarkably para-selective (e.g. 7 + 8 → 11).

Arylation of Olefins by Arylazo Aryl Sulfones under Palladium(0) Catalysis

Palladium(0)-catalyzed reaction of arylazo aryl sulfones with olefins in benzene at 80 deg C gave aryl-substituted olefins in good yield.Diarylpalladium(II) species was proposed as an intermediate in this reaction.