55322-48-0

Upstream product

• 122-97-4 3-Phenyl-1-propanol 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 22818-69-5 (3-nitropropyl)benzene 
• 107-21-1 ethylene glycol 
• 100-51-6 benzyl alcohol 
• 100-42-5 styrene 
• 590-29-4 potassium formate 
• 4119-41-9 1-iodo-3-phenylpropan 

Downstream Products

• 22767-96-0 Benzyl 3-phenylpropionate 
• 15814-45-6 allyl 3-phenylpropionate 
• 1197385-37-7 C₁₇H₁₇NO₂ 
• 2116-64-5 4-(2-phenylethyl)pyridine 
• 2116-62-3 2-(2-phenylethyl)pyridine 
• 1401522-30-2 4-[(1-hydroxy-3-oxo-1-phenethylisoindol-2-yl)methyl]phenyl acetate 
• 1401522-48-2 C₂₃H₁₉NO₂ 
• 131523-29-0 2-(4-hydroxybenzyl)-3-<(E)-2-phenylethylidene>-1-isoindolinone 

Relevant academic research and scientific papers

Synthesis of α-Hydroxy Acids via Dehydrogenative Cross-Coupling of a Sustainable C2 Chemical (Ethylene Glycol) with Alcohols

Ir(NHC) (NHC, N-heterocyclic carbene)-catalyzed dehydrogenative coupling of sustainable ethylene glycol and various bioalcohols can produce industrially valuable α-hydroxy acids (AHAs). This study is the first to report the sustainable synthesis of higher Cn AHAs, in addition to glycolic acid (C2 AHA) and lactic acid (C3 AHA). This catalytic system can be recycled to the seventh cycle while maintaining good yields. A reaction mechanism, including facile dehydrogenation of each alcohol and fast cross-coupling of dehydrogenated aldehydes forming products, was proposed based on 18O- and 2H-labeling experiments and electron spray ionization-mass spectrometry (ESI-MS) and NMR spectral analyses.

Photoinduced Hydrocarboxylation via Thiol-Catalyzed Delivery of Formate across Activated Alkenes

Herein we disclose a new photochemical process to prepare carboxylic acids from formate salts and alkenes. This redox-neutral hydrocarboxylation proceeds in high yields across diverse functionalized alkene substrates with excellent regioselectivity. This operationally simple procedure can be readily scaled in batch at low photocatalyst loading (0.01% photocatalyst). Furthermore, this new reaction can leverage commercially available formate carbon isotologues to enable the direct synthesis of isotopically labeled carboxylic acids. Mechanistic studies support the working model involving a thiol-catalyzed radical chain process wherein the atoms from formate are delivered across the alkene substrate via CO2?- as a key reactive intermediate.

Autoinductive conversion of α,α-diiodonitroalkanes to amides and esters catalysed by iodine byproducts under O2

Studies to convert nitroalkanes into amides and esters using I2 and O2 revealed in situ-generated iodine species facilitate the homolytic C-I bond cleavage of α,α-diiodonitroalkanes, arguably in an autoinductive or autocatalytic manner. Consequently, we devised a rapid and economical I2/O2-based method to synthesise sterically hindered esters directly from primary nitroalkanes.

Iridium catalysts for acceptorless dehydrogenation of alcohols to carboxylic acids: Scope and mechanism

We introduce iridium-based conditions for the conversion of primary alcohols to potassium carboxylates (or carboxylic acids) in the presence of potassium hydroxide and either [Ir(2-PyCH2(C4H5N2))(COD)]OTf (1) or [Ir(2-PyCH2PBu2t)(COD)]OTf (2). The method provides both aliphatic and benzylic carboxylates in high yield and with outstanding functional group tolerance. We illustrate the application of this method to a diverse variety of primary alcohols, including those involving heterocycles and even free amines. Complex 2 reacts with alcohols to form the crystallographically characterized catalytic intermediates [IrH(η1,η3-C8H12)(2-PyCH2PtBu2)] (2a) and [Ir2H3(CO)(2-PyCH2PtBu2){μ-(C5H3N)CH2PtBu2}] (2c). The unexpected similarities in reactivities of 1 and 2 in this reaction, along with synthetic studies on several of our iridium intermediates, enable us to form a general proposal of the mechanisms of catalyst activation that govern the disparate reactivities of 1 and 2, respectively, in glycerol and formic acid dehydrogenation. Moreover, careful analysis of the organic intermediates in the oxidation sequence enable new insights into the role of Tishchenko and Cannizzaro reactions in the overall oxidation.

Surfactant-mediated solvent-free dealkylative cleavage of ethers and esters and trans-alkylation under neutral conditions

A simple, surfactant-mediated, one-pot, solvent-free dealkylative cleavage of aryl ethers and esters followed by subsequent optional trans-alkylation under essentially neutral conditions has been developed.

METAL-CATALYZED SIMULTANEOUS PRODUCTION OF HYDROGEN AND ALKALINE SALTS OF ORGANIC ACIDS

Metal catalysis of the dehydrogenation of primary alcohols to alkaline salts of the corresponding organic acids is described.Conditions (120-170 deg C) are much milder than those required by the uncatalyzed reactions (220-260 deg C).Hydrogen is evolved in the ratio of two molecules per molecule of alcohol.