2516-22-5

Upstream product

• 100-42-5 styrene 
• 60-12-8 2-phenylethanol 
• 50742-77-3 2-benzoyl-5-phenyl-2H-1,3-oxathiole 
• 14629-58-4 trimethyl(phenethyloxy)silane 
• 799254-89-0 (S)-1-phensylethyl diphenykphosphinate 
• 50742-76-2 benzoyl-(2,5-dihydrothiophenio)methanide 
• 70-11-1 α-bromoacetophenone 
• 1445-91-6 (S)-1-phenylethanol 
• 74-85-1 ethene 
• 768-32-1 trimethylphenylsilane 
• 98-85-1 1-Phenylethanol 
• 913542-40-2 (1S)-(1-phenylethoxy)di(phenyl)phosphine 
• 69520-31-6 1-phenacyl-2,5-dihydrothiophenium bromide 
• 864298-61-3 (S)-1-phenylethyl P,P-diphenyl-N-(methanesulfonyl)phosphinimidate 

Downstream Products

• 100-41-4 ethylbenzene 

Relevant academic research and scientific papers

Ruthenium-catalyzed addition reaction of alcohols across olefins

2-Phenylethanol was added to olefins catalyzed by ruthenium catalytic system Cp*RuCl2(PPh3)/2AgOTf in toluene. This reaction proceeded without β-hydride elimination, giving saturated ethers in good yields.

Zirconium-catalysed direct substitution of alcohols: enhancing the selectivity by kinetic analysis

Kinetic analysis was used as a tool for rational optimization of a catalytic, direct substitution of alcohols to enable the selective formation of unsymmetrical ethers, thioethers, and Friedel-Crafts alkylation products using a moisture-tolerant and commercially available zirconium complex (2 to 8 mol%). Operating in air and in the absence of dehydration techniques, the protocol furnished a variety of products in high yields, including glycosylated alcohols and sterically hindered ethers. In addition, the kinetic studies provided mechanistic insight into the network of parallel transformations that take place in the reaction, and helped to elucidate the nature of the operating catalyst.

Oxidative 1,2-Difunctionalization of Ethylene via Gold-Catalyzed Oxyarylation

Under the conditions of oxidative gold catalysis, exposure of ethylene to aryl silanes and alcohols generates products of 1,2-oxyarylation. This provides a rare example of a process that allows catalytic differential 1,2-difunctionalization of this feedstock chemical.

Direct and efficient synthesis of unsymmetrical ethers from alcohols catalyzed by Fe(HSO4)3 under solvent-free conditions

Highly efficient Fe(HSO4)3 catalyzed etherification of primary, secondary and tertiary benzylic alcohols with primary and secondary aliphatic alcohols is reported. The reaction affords unsymmetrical benzyl ethers in good to excellent yields under solvent-free conditions.

Organohalide-catalyzed dehydrative O-alkylation between alcohols: A facile etherification method for aliphatic ether synthesis

Organohalides are found to be effective catalysts for dehydrative O-alkylation reactions between alcohols, providing selective, practical, green, and easily scalable homo- and cross-etherification methods for the preparation of useful symmetrical and unsymmetrical aliphatic ethers from the readily available alcohols. Mechanistic studies revealed that organohalides are regenerated as reactive intermediates and recycled to catalyze the reactions.

Breaking the dichotomy of reactivity vs. chemoselectivity in catalytic SN1 reactions of alcohols

The inability to decouple Lewis acid catalysis from undesirable Bronsted acid catalysed side reactions when water or other protic functional groups are necessarily present has forced chemists to choose between powerful but harsh catalysts or poor but mild

Iron(III) triflimide as a catalytic substitute for gold(I) in hydroaddition reactions to unsaturated carbon-carbon bonds

In this work it is shown that iron(III) and gold(I) triflimide efficiently catalyze the hydroaddition of a wide array of nucleophiles including water, alcohols, thiols, amines, alkynes, and alkenes to multiple C-C bonds. The study of the catalytic activity and selectivity of iron(III), gold(I), and Bronsted triflimides has unveiled that iron(III) triflimide [Fe(NTf 2)3] is a robust catalyst under heating conditions, whereas gold(I) triflimide, even stabilized by PPh3, readily decomposes at 80 °C and releases triflimidic acid (HNTf2) that can catalyze the corresponding reaction, as shown by in situ 19F, 15N, and 31P NMR spectroscopy. The results presented here demonstrate that each of the two catalyst types has weaknesses and strengths and complement each other. Iron(III) triflimide can act as a substitute of gold(I) triflimide as a catalyst for hydroaddition reactions to unsaturated carbon-carbon bonds. Lewis and Bronsted catalysis: It is shown that iron(III) catalyses as efficiently as gold(I) the hydroaddition of a wide array of nucleophiles, including water, alcohols, thiols, amines, alkynes, and alkenes, to multiple C-C bonds (see scheme). Copyright

CATALYTIC C-H BOND ACTIVATION FOR THE SYNTHESIS OF ETHERS AND THIOETHERS

Disclosed is a method for the transition metal-mediated oxidation of C-H bonds to form C-0 or C-S bonds. The methods are useful for the formation of ethers (R-OR') from alcohols, R'OH, and sp3 -hybridized C-H bonds in substrates, R-H. Aryl or heteroaryl acetates may also be used for C-H to C-OAr bond formation. The methods are also useful in the preparation of C-S bonds from acetyl-protected thiols, MeC(0)SR, and disulfides, RSSR. Advantageously, the methods minimize reaction steps, the handling of oxidized intermediates, and environmental impact.

A convenient method for the synthesis of dialkyl ethers by alkylation of alcohols using phosphinimidates in the presence of a catalytic amount of trimethylsilyl triflate

An alkylation reaction of alcohols with alkyl N-(methylsulfonyl) diphenylphosphinimidates proceeded smoothly in the presence of a catalytic amount of trimethylsilyl triflate (Me3SiOTf) in DME at room temperature and the corresponding ethers were afforded in good to high yields. An alkyl N-(methylsulfonyl)diphenylphosphinimidate can be prepared easily from an alkyl diphenylphosphinite and methanesulfonyl azide, and is isolated without tedious operation. Moreover, it is easy to handle and can be stored for several months at room temperature because of its air- and moisture-resistant character. Also, one-pot tertiary alkylations of alcohols by using t-alkyl diphenylphosphinites and diphenoxyphosphoryl azide proceeded efficiently in the presence of a catalytic amount of Me3SiOTf in cyclohexane/CH 2Cl2 at 0°C or -10°C, and gave the corresponding tertiary alkyl ethers in good yields. By following these methods, various ethers having alkali-sensitive functional groups can be prepared easily.

Hydroamination and hydroalkoxylation catalyzed by triflic acid. Parallels to reactions initiated with metal triflates

(Chemical Equation Presented) Intermolecular additions of the O-H bonds of phenols and alcohols and the N-H bonds of sulfonamides and benzamide to olefins catalyzed by 1 mol % of triflic acid and studies to define the relationship between these reactions and those catalyzed by metal triflates are reported. Cyclization of an alcohol containing pendant monosubstituted and trisubstituted olefins catalyzed by either triflic acid or metal triflates form products from addition to the more substituted olefin, and additions of tosylamide catalyzed by triflic acid or metal triflates form indistinguishable ratios of the two N-alkyl sulfonamides.