87456-64-2

Upstream product

• 27126-76-7 [hydroxy(tosyloxy)iodo]benzene 
• 93-55-0 1-phenyl-propan-1-one 
• 104-15-4 toluene-4-sulfonic acid 
• 440365-99-1 3,5-bis(trifluoromethyl)-1-[hydroxy(tosyloxy)iodo]benzene 
• 93-54-9 1-Phenyl-1-propanol 
• 73177-96-5 <(hydroxy)(tosyloxy)iodo>-p-toluene 
• 25370-97-2 O-(p-toluenesulfonyl)-N-methylhydroxylamine 
• 159950-96-6 1-(p-methylbenzenesulfonyloxy)-1,2-benziodoxol-3(1H)-one 
• 4518-65-4 (1-methoxyprop-1-en-1-yl)benzene 
• 13266-91-6 (Z)-1-phenylprop-1-en-1-yl acetate 
• 1430119-54-2 (Z)-1-phenylprop-1-en-1-yl 4-methylbenzenesulfonate 
• 1227710-56-6 hydroxy-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)iodonium toluene-4-sulfonate 
• 25370-96-1 O-(p-toluenesulfonyl)-N-tert-butoxycarbonyl-N-methylhydroxylamine 

Downstream Products

• 6084-15-7 2-iodo-1-phenylpropan-1-one 
• 143088-27-1 Selenophosphoric acid O,O'-diethyl ester Se-(1-methyl-2-oxo-2-phenyl-ethyl) ester 
• 34658-68-9 3-methyl-2-phenyl-1H-imidazo[1,2-a]pyridine 
• 61001-08-9 3-methyl-2-phenylimidazo[2,1-a]isoquinoline 
• 20177-86-0 2-(1-methyl-2-oxo-2-phenylethylsulfanyl)-1-phenyl-propan-1-one 
• 52306-27-1 (cis)-2-methyl-1-phenylcyclopropan-1-ol 
• 52306-27-1 2-methyl-1-phenyl-1-cyclopropanol 
• 71908-02-6 (2SR,3RS)-3-hydroxy-2-methyl-1,3-diphenylpropan-1-one 
• 71908-03-7 (2SR,3RS)-2-methyl-1,3-diphenyl-3-hydroxypropan-1-one 
• 93-55-0 1-phenyl-propan-1-one 
• 81111-93-5 1-phenyl-2-(p-toluenesulfonyloxy)-1-propanone dimethyl acetal 
• 6084-17-9 2-chloro-1-phenylpropan-1-one 
• 1210046-21-1 1-phenyl-2-(4-phenyl-[1,2,3]triazol-1-yl)-propan-1-one 
• 93020-55-4 5-methyl-4-phenyl-2-(N-phenylamino)thiazole 

Relevant academic research and scientific papers

Chiral Ligands in Hypervalent Iodine Compounds: Synthesis and Structures of Binaphthyl-Based λ3-Iodanes

Several novel binaphthyl-based chiral hypervalent iodine(III) reagents have been prepared and structurally analysed. Various asymmetric oxidative reactions were applied to evaluate the reactivities and stereoselectivities of those reagents. Moderate to excellent yields were observed; however, very low stereoselectivities were obtained. NMR experiments indicated that these reagents are very easily hydrolysed in either chloroform or DMSO solvents leading to the limited stereoselectivities. It is concluded that the use of chiral ligands is an unsuccessful way to prepare efficient stereoselective iodine(III) reagents.

Design and synthesis of Fmoc-SPPS-ready iodoarene amino acid pre-catalysts and their reactivity in the catalytic oxytosylation of ketones

A small suite of iodo-aryl amide containing amino acids were synthesized and assessed as catalysts for the hypervalent iodine(III) mediated α-oxytosylation of ketones. The efficiency of each catalyst was determined by comparing the relative rates of catalysis in the direct α-oxytosylation of propiophenone. In addition, these catalysts can be easily converted to congeners that are suitable for Fmoc-solid phase peptide synthesis for facile incorporation into a chiral peptide framework. This work facilitates the broader goal of our program to develop peptide-based enantioselective catalysts for hypervalent iodine chemistry.

Continuous-Flow Electrochemical Generator of Hypervalent Iodine Reagents: Synthetic Applications

An efficient and reliable electrochemical generator of hypervalent iodine reagents has been developed. In the anodic oxidation of iodoarenes to hypervalent iodine reagents under flow conditions, the use of electricity replaces hazardous and costly chemical oxidants. Unstable hypervalent iodine reagents can be prepared easily and coupled with different substrates to achieve oxidative transformations in high yields. The unstable, electrochemically generated reagents can also easily be transformed into classic bench-stable hypervalent iodine reagents through ligand exchange. The combination of electrochemical and flow-chemistry advantages largely improves the ecological footprint of the overall process compared to conventional approaches.

Synthesis, characterisation, and reactivity of novel pseudocyclic hypervalent iodine reagents with heteroaryl carbonyl substituents

Two new hypervalent iodine reagents containing furan and thiophene moieties in addition to a carbonyl group in the vicinity of the iodine atom were synthesised and characterised. The X-ray analysis of both compounds revealed a strong intramolecular contact between the carbonyl oxygen and the hypervalent iodine atom with tosylate as a counter ion. The two reagents showed a broad range of synthetic applications and proved to be versatile oxidizing agents.

Relative Rate Profiles of Functionalized Iodoarene Catalysts for Iodine(III) Oxidations

A series of rate studies were conducted to evaluate the steric and electronic properties that govern the reactivity of iodoarene amide catalysts in the α-oxytosylation of propiophenone. A meta-substituted benzamide catalyst emerged as the most reactive. This catalyst was employed in the α-oxytosylation of a series of substituted propiophenones, returning the α-tosyloxy ketone products in excellent isolated yield.

General Method for the Preparation of Electron-Deficient Imidazo[1,2-a]pyridines and Related Heterocycles

A new annulation method for the preparation of the imidazo[1,2-a]pyridine ring system under mild conditions is presented. Treatment of a 2-aminopyridine with a dimethylketal tosylate in acetonitrile at elevated temperature (80-140°C) in the presence of catalytic Sc(OTf)3 provides the imidazo[1,2-a]pyridine product in good yield. The annulation method is broadly applicable to electron-poor 2-aminopyridines and displays a complementary profile to the classic preparation of the imidazo[1,2-a]pyridine ring system by reaction of a bromoketone with electron-rich and -neutral substrates. The scope of the process and mechanistic considerations are discussed.

Enantioselective Iodine(III)-Mediated Synthesis of α-Tosyloxy Ketones: Breaking the Selectivity Barrier

The development of practical methods to access chiral nonracemic α-substituted ketones is of particular importance due to their ubiquitous nature. Unprecedented levels of enantioselectivity are reported for the synthesis of α-tosyloxy ketones, using enol esters and chiral iodine(III) reagents. The reaction can be performed under both stoichiometric and catalytic conditions. These results suggest widely different reaction mechanisms for the reaction of ketones versus enol esters, supporting recent computational insights.

Study of the Reactivity of [Hydroxy(tosyloxy)iodo]benzene Toward Enol Esters to Access α-Tosyloxy Ketones

The reactivity of enol esters toward [hydroxy(tosyloxy)iodo]benzene (HTIB) was assessed. These substrates were found to be rapidly converted in high yields to their corresponding α-tosyloxy ketones. This transformation demonstrates that these substrates can act as ketone surrogates. The scope of the method was investigated and aromatic, aliphatic, and cyclic enol esters were found to be suitable substrates for the reaction. The relative reactivity of a model substrate toward HTIB and m-CPBA was investigated, and it was found that the reaction could be performed under catalytic conditions.

Effective α-tosyloxylation of ketones using 1,1,1-trifluoro-2-iodoethane as catalyst

With 1,1,1-trifluoro-2-iodoethane as catalyst, a novel and efficient procedure has been developed for preparation of α-tosyloxyketones from ketones. In this protocol, 1,1,1-trifluoro-2-iodoethane is first oxidized by m-chloroperbenzoic acid to a hypervale

Oxidative breakdown of iodoalkanes to catalytically active iodine species: A case study in the α-tosyloxylation of ketones

Catalysis of the oxidative processes by iodoarenes has become a promising direction in synthesis. The mechanism, involving the well-known isolable hypervalent iodine species, is generally limited to aromatic iodides, since the corresponding aliphatic spec