22509-78-0

Upstream product

• 563-52-0 2-chloro-3-butene 
• 108-95-2 phenol 
• 22037-73-6 3-bromo-1-butene 
• 504-61-0 (E)-but-2-enol 
• 598-32-3 2-hydroxy-3-butene 
• 91668-28-9 2-butenyl phenyl carbonate 
• 122898-55-9 1-methyl-propenyl phenyl carbonate 
• 100-67-4 potassium phenolate 
• 106-99-0 buta-1,3-diene 
• 4894-61-5 trans-but-2-enyl chloride 
• 122898-53-7 2-butenyl phenyl carbonate 

Downstream Products

• 14004-15-0 2-crotylphenol 
• 4050-45-7 trans-2-hexene 
• 935-00-2 trans-4-phenyl-2-butene 
• 36617-88-6 (R)-3-phenyl-1-butene 
• 58717-85-4 (S)-3-phenyl-1-butene 
• 18272-63-4 2-(but-3-en-2-yl)phenol 
• 230293-43-3 2,3-Dihydro-3-methylbenzofurane-2-carboxylic acid 
• 3180-09-4 ortho-butylphenol 

Relevant academic research and scientific papers

Green Organocatalytic Synthesis of Dihydrobenzofurans by Oxidation-Cyclization of Allylphenols

A green and cheap protocol for the synthesis of dihydrobenzofurans via an organocatalytic oxidation of o -allylphenols is presented. The use of 2,2,2-trifluoroacetophenone and H 2 O 2 as the oxidation system, leads to a highly useful synthetic method, where a variety of substituted o -allylphenols were cyclized in high yields..

Origins of Regioselectivity in Iridium Catalyzed Allylic Substitution

Detailed studies on the origin of the regioselectivity for formation of branched products over linear products have been conducted with complexes containing the achiral triphenylphosphite ligand. The combination of iridium and P(OPh)3 was the first catalytic system shown to give high regioselectivity for the branched product with iridium and among the most selective for forming branched products among any combination of metal and ligand. We have shown the active catalyst to be generated from [Ir(COD)Cl]2 and P(OPh)3 by cyclometalation of the phenyl group on the ligand and have shown such species to be the resting state of the catalyst. A series of allyliridium complexes ligated by the resulting P,C ligand have been generated and shown to be competent intermediates in the catalytic system. We have assessed the potential impact of charge, metal-iridium bond length, and stability of terminal vs internal alkenes generated by attack at the branched and terminal positions of the allyl ligand, respectively. These factors do not distinguish the regioselectivity for attack on allyliridium complexes from that for attack on allylpalladium complexes. Instead, detailed computational studies suggest that a series of weak, attractive, noncovalent interactions, including interactions of H-bond acceptors with a vinyl C - H bond of the alkene ligand, favor formation of the branched product with the iridium catalyst. This conclusion underscores the importance of considering attractive interactions, as well as repulsive steric interactions, when seeking to rationalize selectivities.

Development of a 4,4′-biphenyl/phosphine-based COF for the heterogeneous Pd-catalysed telomerisation of 1,3-butadiene

The improved synthesis, characterisation and application of a microporous 4,4′-biphenyl/phosphine-based covalent organic framework (COF) for the heterogeneous Pd-catalysed telomerisation of 1,3-butadiene with phenol and glycerol are presented. The solid polyphosphine is amorphous, microporous and an excellent support for Pd(acac)2. Solid-state NMR and DRIFT analysis of materials of varying Pd-loading show that bis-phosphine complexes of palladium are preferably formed. Under solvent- and base-free conditions, high conversions and selectivities are obtained for this catalyst material with both phenol and glycerol as substrates. The product selectivity, with both butenylation and telomerisation activity observed with phenol, can be tuned by variation of the metal loading. For glycerol it is shown that the selectivity to the undesired tri telomer is low under all applied conditions and, remarkably, that the heterogeneous catalyst outperforms its homogeneous PPh 3-based counterpart.

Regioselective iron-catalyzed decarboxylative allylic etherification

[Chemical Equation Presented] An anionic iron complex catalyzes the decarboxylative allylation of phenols to form allylic ethers in high yield. The allylation is regioselective rather than regiospecific. This suggests that the allylation proceeds through π-allyl iron intermediates in contrast to related allylations of carbon nucleophiles that have been proposed to proceed via π-allyl complexes. Ultimately, iron catalysts have the potential to replace more expensive palladium catalysts that are typically utilized for decarboxylative couplings.

Ruthenium-catalyzed o-allylation of phenols from allylic chlorides via cationic [Cp*(η3-allyl)(MeCN)RuX][PF6] complexes

The [Cp*(MeCN)3Ru(II)][PF6] complex is an efficient catalyst precursor for the O-allylation of phenols with allylic chlorides in the presence of K2CO3 under mild conditions. This ruthenium precursor affords branched allyl aryl ethers according to a regioselective reaction, which contrasts with the uncatalyzed nucleophilic substitution from the same substrates. Stable (η3-allyl)Ru(IV) cationic complexes resulting from the reaction of [Cp*(MeCN) 3Ru][PF6] with allylic halides were identified as intermediate catalytic species. An X-ray structure determination of the complex [Cp*(MeCHCHCH2)(MeCN)RuBr] [PF6] disclosed an (endo-trans-MeCHCHCH2) allylic ligand. The structural information obtained from the study of Cp*(allyl)Ru(IV) complexes indicated that electronic effects at the coordinated allylic ligand likely account for the better regioselectivity obtained from cinnamyl chloride as compared to aliphatic allylic chlorides.

Copper(II)-catalyzed ether synthesis from aliphatic alcohols and potassium organotrifluoroborate salts

(Matrix presented) A protocol for the copper(II)-catalyzed etherification of aliphatic alcohols under mild and essentially neutral conditions is described. Air- and moisture-stable potassium alkenyl- and aryltrifluoroborate salts undergo cross-coupling with a variety of aliphatic primary and secondary alcohols and phenols, and are tolerant of a range of functional groups. The optimized conditions utilize catalytic copper(II) acetate with 4-(dimethylamino)pyridine as ligand in the presence of 4 A molecular sieves under an atmosphere of oxygen.

SmI2/water/amine mediates cleavage of allyl ether protected alcohols: application in carbohydrate synthesis and mechanistic considerations.

[reaction: see text]. SmI2/H2O/amine provides selective cleavage of unsubstituted allyl ethers in good to excellent yields. This method is therefore useful in deprotection of alcohols and carbohydrates.

Synthesis of allylic aryl ethers via palladium-catalyzed decarboxylation of allylic aryl carbonates

Allylic aryl ethers are readily prepared in high yield by the palladium-catalyzed decarboxylation of allylic aryl carbonates.

α-Adrenoreceptor Reagents. 2. Effects of Modification of the 1,4-Benzodioxan Ring System on α-Adrenoreceptor Activity

Modification of the 1,4-benzodioxan ring present in RX 781094 (1) has not previously been considered.This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives.The dihydroxybenzofuranylimidazoline compound 7 is the only analogue possesing presynaptic antagonist potency and selectivity comparable to that of 1.In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series.Many derivatives, as well as the parent compound 7, were found to possess presynaptic α2-adrenoreceptor antagonist and postsynaptic α1-adrenoreceptor partial agonist properties.Two of the selective presynaptic antagonists,13 and 14, possess greater potency and selectivity than that possessed by 1.The 5-chloro derivative 25 is twice as potent as 1 after oral administration but only about half as potent when given intravenously.