5370-67-2

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 67-56-1 methanol 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 124-41-4 sodium methylate 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 1019651-81-0 3-methoxy-1-phenyl-3-(2-thienyl)propan-1-one 
• 26059-21-2 phenyl-thiophen-2-yl-methanol 
• 31330-51-5 ethyl (E)-2-cyano-3-(2-thienyl)-2-propenoate 
• 1388830-39-4 2-phenyl-3-(2-thienylmethyl)pyrrole 
• 1388830-66-7 2-phenyl-3-(2-thienylmethylidene)-1-pyrroline 
• 192990-74-2 5-{5-[(E)-2-(4-Dimethylamino-phenyl)-vinyl]-thiophen-2-ylsulfanyl}-thiophene-2-carbaldehyde 
• 98-03-3 thiophene-2-carbaldehyde 

Relevant academic research and scientific papers

Multicomponent Aromatic and Benzylic Mannich Reactions through C?H Bond Activation

Multicomponent Mannich reactions through C?H bond activation are described. These transformations allowed for the straightforward generation of densely substituted benzylic and homo-benzylic amines in good yields. The reaction involves a reaction between two transient species: an organometallic species, generated by transition-metal-catalyzed sp2 or sp3 C?H bond activation and an in situ generated imine. The use of an acetal as an aldehyde surrogate was found essential for the reaction to proceed. The process could be successfully applied to RhIII-catalyzed sp2 C?H bond functionalization and extended to CuII-catalyzed sp3 C?H bond functionalization.

Unique chemoselective Mukaiyama aldol reaction of silyl enol diazoacetate with aldehydes and acetals catalyzed by MgI2 etherate

Functionalized diazo acetoacetates are prepared by an efficient Mukaiyama aldol reaction between 3-TBSO-2-diazo-3-butenoate with aldehydes and acetals under mild reaction conditions. A variety of substituted aldehydes and the corresponding acetals are both accessible in good to excellent yields through this methodology. MgI2 etherate (MgI2·(OEt2)n) is the preferred catalyst and, the addition proceeds without decomposition of the diazo moiety. In addition, this MgI2·(OEt2)n-catalyzed Mukaiyama aldol reaction shows unique chemoselectivity towards aldehydes and acetals.

Nickel-Catalyzed Chemoselective Acetalization of Aldehydes With Alcohols under Neutral Conditions

A molecularly defined NiII-complex catalyzing the chemoselective acetalization of aldehydes with alcohols under neutral conditions is reported. The reaction is general, efficient and showed a wide substrate scope (including aliphatic aldehydes) as well as excellent functional group tolerance. Reusability of the present nickel catalyst is also demonstrated.

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.

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.

Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions

We report here on the use of ethyl nitroacetate as a glycine template to produce α-amino esters. This started with a study of its condensation with various arylacetals to give ethyl 3-aryl-2-nitroacrylates followed by a reduction (NaBH4 and then zinc/HCl) into α-amino esters. The scope of this method was explored as well as an alternative with arylacylals instead. We also focused on various [2 + 3] cycloadditions, one leading to a spiroacetal, which led to the undesired ethyl 5-(benzamidomethyl)isoxazole-3-carboxylate. The addition of ethyl nitroacetate on a 5-methylene-4,5-dihydrooxazole using cerium(IV) ammonium nitrate was also explored and the synthesis of other oxazole-bearing α-amino esters was achieved using gold(I) chemistry.

Ru(II)-functionalized SBA-15 as highly chemoselective, acid free and sustainable heterogeneous catalyst for acetalization of aldehydes and ketones

Combining electron deficient Ru(II) coordination sites with organofunctionalized SBA-15, (L)Ru(II)@SBA-15, result in a mild, neutral, water scavenger free and chemo-selective acetalization catalyst for cyclic/acyclic acetals. Vacant coordination sites of ruthenium in (L)Ru(II)@SBA-15 activates protecting groups as well as reactants simultaneously and restricts the reverse acetalization reaction. Synthesized (L)Ru(II)@SBA-15 catalyst has been thoroughly characterized and act as competitive catalyst compared to conventional acid catalysts. (L)Ru(II)@SBA-15 performs high catalytic activity as well as selectivity within 20 min with high TOF. The catalyst can be recycled and reaction parameters are optimized.

Phosphorylated Polyacrylonitrile Fibers as an Efficient and Greener Acetalization Catalyst

A novel solid acid catalyst (PANEAPF) is developed by immobilization of phosphoric acid on polyacrylonitrile fiber through covalent bonding. Various characterization techniques such as elemental analysis (EA), X-ray photoelectron spectroscopy (XPS), Fourier transform infrared spectroscopy (FTIR), etc. are utilized to confirm the successful grafting and the stability of the fiber catalysts during application. PANEAPF shows high catalytic activity in the acetalization of aldehydes owing to the high utilization efficiency of its functionalized acid sites. In addition, the strong polarity micro-environment in the surface layers of PANEAPF make it highly suitable for catalytic application in both water and alcohol. Furthermore, the fiber catalyst can be applied to the acetalization of aldehydes in a continuous-flow process at room temperature, and shows excellent reactivity and superior recyclability (over 20 times). The many advantages of PANEAPF such as simple preparation, convenient regulation of acid amount, high durability, and eco-friendly process make it very attractive for fixed-bed reactors in the chemical industry.

A bifunctional cerium phosphate catalyst for chemoselective acetalization

Acid-base solid catalysts synthesized with structurally controlled uniform active sites can lead to unique catalysis. In this study, a CePO4 catalyst was synthesized using a hydrothermal method and found to exhibit high catalytic performance for the chemoselective acetalization of 5-hydroxymethylfurfural with alcohols, in sharp contrast to other homogeneous and heterogeneous acid and/or base catalysts. In the presence of CePO4, various combinations of carbonyl compounds and alcohols are efficiently converted into the corresponding acetal derivatives in good to excellent yields. Mechanistic studies show that CePO4 most likely acts as a bifunctional catalyst through the interaction of uniform Lewis acid and weak base sites with 5-hydroxymethylfurfural and alcohol molecules, respectively, which results in high catalytic performance.

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.