77821-95-5

Upstream product

• 104-54-1 3-Phenylpropenol 
• 75-98-9 Trimethylacetic acid 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 3282-30-2 pivaloyl chloride 
• 100-42-5 styrene 
• 53064-79-2 iodomethyl pivaloate 

Downstream Products

• 1350563-85-7 (C₆H₅CHCH₃(CH₂CHCHC₆H₅))Cr(CO)3 
• 19752-27-3 phenylallyl(tributyl)stannane 
• 134792-03-3 2-(cinnamylthio)benzo[d]thiazole 
• 122322-96-7 5-(cinnamylthio)-1-phenyl-1H-tetrazole 
• 1720-32-7 1,6-diphenyl-hexa-1,3,5-triene 
• 27962-45-4 2-hydroxy-1,2,5-triphenyl-pent-4-en-1-one 

Relevant academic research and scientific papers

Copper-Catalyzed Transfer Hydrodeuteration of Aryl Alkenes with Quantitative Isotopomer Purity Analysis by Molecular Rotational Resonance Spectroscopy

A copper-catalyzed alkene transfer hydrodeuteration reaction that selectively incorporates one hydrogen and one deuterium atom across an aryl alkene is described. The transfer hydrodeuteration protocol is selective across a variety of internal and terminal alkenes and is also demonstrated on an alkene-containing complex natural product analog. Beyond using 1H, 2H, and 13C NMR analysis to measure reaction selectivity, six transfer hydrodeuteration products were analyzed by molecular rotational resonance (MRR) spectroscopy. The application of MRR spectroscopy to the analysis of isotopic impurities in deuteration chemistry is further explored through a measurement methodology that is compatible with high-throughput sample analysis. In the first step, the MRR spectroscopy signatures of all isotopic variants accessible in the reaction chemistry are analyzed using a broadband chirped-pulse Fourier transform microwave spectrometer. With the signatures in hand, measurement scripts are created to quantitatively analyze the sample composition using a commercial cavity enhanced MRR spectrometer. The sample consumption is below 10 mg with analysis times on the order of 10 min using this instrument - both representing order-of-magnitude reduction compared to broadband MRR spectroscopy. To date, these measurements represent the most precise spectroscopic determination of selectivity in a transfer hydrodeuteration reaction and confirm that product regioselectivity ratios of >140:1 are achievable under this mild protocol.

Visible Light-Induced Room-Temperature Heck Reaction of Functionalized Alkyl Halides with Vinyl Arenes/Heteroarenes

The first visible light-induced Pd-catalyzed Heck reaction of α-heteroatom substituted alkyl iodides and -bromides with vinyl arenes/heteroarenes has been developed. This transformation efficiently proceeds at room temperature and enables synthesis of valuable functionalized allylic systems, such as allylic silanes, boronates, germanes, stannanes, pivalates, phosphonates, phthalimides, and tosylates from the corresponding α-substituted methyl iodides. Notably, synthesis of the latter substrates failed under existing thermally induced Pd-catalyzed conditions, which highlights the importance of visible light for this transformation.

Ni-Catalyzed Stannylation of Aryl Esters via C?O Bond Cleavage

A Ni-catalyzed stannylation of aryl esters with air- and moisture-insensitive silylstannyl reagents via Csp2 ?O cleavage is described. This protocol is characterized by its wide scope, including challenging combinations, thus enabling access to versatile building blocks and orthogonal C?heteroatom bond formations.

Catalytic nucleophilic acyl substitution of anhydrides by amphoteric vanadyl triflate

Figure presented Among four vanadyl species examined, vanadyl triflate was the most efficient catalyst to facilitate nucleophilic acyl substitution of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. By using mixed-anhydride technique, one can achieve oleate and peptide syntheses. In marked contrast to common metal Inflates, the amphoteric character of the V=O unit in vanadyl species was proven to be responsible for the catalytic profile in this process.