5784-65-6

Upstream product

• 100-52-7 benzaldehyde 
• 100-51-6 benzyl alcohol 
• 614-45-9 tert-Butyl peroxybenzoate 
• 14642-79-6 benzyloxy-trimethylsilane 
• 555-16-8 4-nitrobenzaldehdye 
• 351-70-2 benzyl trifluoroacetate 
• 20194-18-7 sodium phenyl-methanolate 
• 774-48-1 (diethoxymethyl)benzene 
• 13959-92-7 benzyl triethylsilyl ether 

Downstream Products

• 100-52-7 benzaldehyde 
• 108-88-3 toluene 
• 119225-80-8 threo-3-benzyloxy-2-methyl-1,3-diphenylpropan-1-one 
• 119225-80-8 erythro-3-benzyloxy-2-methyl-1,3-diphenylpropan-1-one 
• 121097-23-2 (2R,5R)-2-((1S,2R)-1-Benzyl-2-benzyloxy-2-phenyl-ethyl)-5-cyclohexyl-[1,3]dioxolan-4-one 
• 121097-23-2 (2R,5R)-2-((1R,2R)-1-Benzyl-2-benzyloxy-2-phenyl-ethyl)-5-cyclohexyl-[1,3]dioxolan-4-one 
• 6907-59-1 1-benzylisoquinoline 
• 100-51-6 benzyl alcohol 
• 5773-56-8 1,2-Diphenylethanol 
• 103-50-4 dibenzyl ether 
• 120-51-4 benzoic acid benzyl ester 
• 137438-51-8 4-(benzyloxy)-4-phenyl-1-butene 
• 1309647-64-0 C₁₂H₁₄O₄ 
• 111636-13-6 4-hydroxy-4-phenyl-butyric acid ethyl ester 

Relevant academic research and scientific papers

One-step solvent-free aerobic oxidation of aliphatic alcohols to esters using a tandem Sc-Ru?MOF catalyst

Esters are an important class of chemicals in industry. Traditionally, ester production is a multi-step process involving the use of corrosive acids or acid derivatives (e.g. acid chloride, anhydride, etc.). Therefore, the development of a green synthetic protocol is highly desirable. This work reports the development of a metal-organic framework (MOF) supported tandem catalyst that can achieve direct alcohol to ester conversion (DAEC) using oxygen as the sole oxidizing agent under strictly solvent-free conditions. By incorporating Ru nanoparticles (NPs) along with a homogeneous Lewis acid catalyst, scandium triflate, into the nanocavities of a Zr MOF, MOF-808, the compound catalyst, Sc-Ru?MOF-808, can achieve aliphatic alcohol conversion up to 92% with ester selectivity up to 91%. A mechanistic study reveals a unique “via acetal” pathway in which the alcohol is first oxidized on Ru NPs and rapidly converted to an acetal on Sc(iii) sites. Then, the acetal slowly decomposes to release an aldehyde in a controlled manner for subsequent oxidation and esterification to the ester product. To the best of our knowledge, this is the first example of DAEC of aliphatic alcohols under solvent-free conditions with high conversion and ester selectivity.

Breaking C-O Bonds with Uranium: Uranyl Complexes as Selective Catalysts in the Hydrosilylation of Aldehydes

We report herein the possibility to perform the hydrosilylation of carbonyls using actinide complexes as catalysts. While complexes of the uranyl ion [UO2]2+ have been poorly considered in catalysis, we show the potentialities of the Lewis acid [UO2(OTf)2] (1) in the catalytic hydrosilylation of a series of aldehydes. [UO2(OTf)2] proved to be a very active catalyst affording distinct reduction products depending on the nature of the reductant. With Et3SiH, a number of aliphatic and aromatic aldehydes are reduced into symmetric ethers, while iPr3SiH yielded silylated alcohols. Studies of the reaction mechanism led to the isolation of aldehyde/uranyl complexes, [UO2(OTf)2(4-Me2N-PhCHO)3], [UO2(μ-κ2-OTf)2(PhCHO)]n, and [UO2(μ-κ2-OTf)(κ1-OTf)(PhCHO)2]2, which have been fully characterized by NMR, IR, and single-crystal X-ray diffraction.

Access to Wieland-Miescher Diketone-Derived Building Blocks by Stereoselective Construction of the C-9 Quaternary Carbon Center Using the Mukaiyama Aldol Reaction

The Mukaiyama aldol reaction has been used to efficiently install a lateral chain at the C-9 position of the Wieland-Miescher ketone derivative 3 within two steps, representing a shortcut compared to that of the classical sequences. The treatment of the silylated enol ether 8 with a wide range of acetals in the presence of tin tetrachloride led to a the diastereoselective construction of the C-9 quaternary center of 33 new building blocks derived from the Wieland-Miescher ketone derivative 3.

Preparation of acetals from aldehydes and alcohols under basic conditions

A new, simple protocol for the synthesis of acetals under basic conditions from non-enolizable aldehydes and alcohols has been reported. Such reactivity is facilitated by a sodium alkoxide along with a corresponding trifluoroacetate ester, utilizing formation of sodium trifluoroacetate as a driving force for acetal formation. The usefulness of this protocol is demonstrated by its orthogonality with various acid-sensitive protecting groups and by good compatibility with functional groups, delivering synthetically useful acetals complementarily to the synthesis under acidic conditions from aldehydes and alcohols.

Phosphine-pyridonate ligands containing octahedral ruthenium complexes: Access to esters and formic acid

The preparation of three well-defined ruthenium complexes arising from phosphine-pyridon-e/-ate ligands is described. Solvent dependent Lewis acidic species formation was observed with these complexes. Selective formation of acetals or esters from primary alcohols was observed in the presence of these catalysts. Preliminary evaluation of these complexes in the base free hydrogenation of carbon dioxide is also reported.

Acetals from primary alcohols with the use of tridentate proton responsive phosphinepyridonate iridium catalysts

The association of the new phosphinepyridonate ligands along with an iridium metallic precursor resulted in the selective acetalization of various primary alcohols via a formal dehydrogenative coupling reaction.

Supported Tetrahedral Oxo-Sn Catalyst: Single Site, Two Modes of Catalysis

Mild calcination in ozone of a (POSS)-Sn-(POSS) complex grafted on silica generated a heterogenized catalyst that mostly retained the tetrahedral coordination of its homogeneous precursor, as evidenced by spectroscopic characterizations using EXAFS, NMR, UV-vis, and DRIFT. The Sn centers are accessible and uniform and can be quantified by stoichiometric pyridine poisoning. This Sn-catalyst is active in hydride transfer reactions as a typical solid Lewis acid. However, the Sn centers can also create Br?nsted acidity with alcohol by binding the alcohol strongly as alkoxide and transferring the hydroxyl H to the neighboring Sn-O-Si bond. The resulting acidic silanol is active in epoxide ring opening and acetalization reactions.

Selective acceptorless conversion of primary alcohols to acetals and dihydrogen catalyzed by the ruthenium(II) complex Ru(PPh3) 2(NCCH3)2(SO4)

The complex bis(acetonitrile)bis(triphenylphosphine)ruthenium(II) sulfate [Ru(PPh3)2(NCCH3)2(SO4)], fully characterized spectroscopically and by a single crystal X-ray study, catalyzes at 110 °C the direct transformation of primary alcohols to the corresponding acetals with liberation of molecular hydrogen. The formation of acetals proceeds via direct substitution of the hydroxy group of the hemiacetal intermediate by an alcohol molecule. The closely related bis(triphenylphosphine) ruthenium(II) acetate [Ru(PPh3)2(OAc)2] catalyzes the conversion of primary alcohols to the corresponding esters rather than acetals. Copyright

Efficient and chemoselective acetalization and thioacetalization of carbonyls and subsequent deprotection using InF3 as a reusable catalyst

An efficient and chemoselective method for preparation of acetals and dithioacetals of aldehydes and their deprotection under catalysis of InF 3 is described.

Catalytic synthesis of γ-alkoxy-α-keto esters

Copper(II) triflate effectively catalyzes the reaction of (trimethylsilyloxy)acrylic esters and acetals to form -alkoxy - keto esters. The reaction proceeds under mild conditions providing products in good to excellent yields. The substrate scope was investigated, and it was demonstrated that the products could be converted into related compounds such as γ-hydroxy -α- keto esters and α-oximes. Georg Thieme Verlag Stuttgart - New York.