100130-55-0

Upstream product

• 100-97-0 hexamethylenetetramine 
• 99848-41-6 1-(bromomethyl)-2-iodo-3-methylbenzene 
• 608-28-6 2,6-dimethyliodobenzene 
• 100959-88-4 (2-iodo-3-methylphenyl)methanol 
• 108078-14-4 2-iodo-3-methylbenzoic acid 
• 4389-45-1 3-methylantranilic acid 

Downstream Products

• 1370697-34-9 1-(2-((4-methoxyphenyl)ethynyl)-3-methylphenyl)-3-phenylprop-2-yn-1-ol 
• 1370697-64-5 C₁₇H₁₄O₂ 
• 1415763-90-4 (4R,5S)-2-(2-iodo-3-methylphenyl)-4-methyl-5-phenyl-4,5-dihydrooxazole 
• 1415763-88-0 (R)-2-(2-iodo-3-methylphenyl)-5-phenyl-4,5-dihydrooxazole 

Relevant academic research and scientific papers

Iodolopyrazolium Salts: Synthesis, Derivatizations, and Applications

The synthesis of iodolopyrazolium triflates via an oxidative cyclization of 3-(2-iodophenyl)-1H-pyrazoles is described. The reaction is characterized by a broad substrate scope, and various applications of these novel cyclic iodolium salts acting as useful synthetic intermediates are demonstrated, in particular in site-selective ring openings. This was finally applied to generate derivatives of the anti-inflammatory drug celecoxib. Their application as highly active halogen-bond donors is shown as well.

F- Nucleophilic-Addition-Induced [3 + 2] Annulation: Direct Access to CF3-Substituted Indenes

An efficient [3 + 2] annulation of (2,2-difluorovinyl)-2-iodoarenes and internal alkynes was developed for the synthesis of 1-(trifluoromethyl)-1H-indenes. The success of this strategy hinges upon a well-balanced process for the generation of two transient reactive species, specifically trifluoroethylsilver and alkenylpalladium intermediates, in the same molecule, as well as a smooth transmetalation step, which delicately joins together these two different metallic intermediates.

Evolution of N-Heterocycle-Substituted Iodoarenes (NHIAs) to Efficient Organocatalysts in Iodine(I/III)-Mediated Oxidative Transformations

The reactivity of ortho-functionalized N-heterocycle-substituted iodoarenes (NHIAs) as organocatalysts in iodine(I/III)-mediated oxidations was systematically investigated in the α-tosyloxylation of ketones as the model reaction. During a systematic catalyst evolution, it was found that NH-triazoles and benzoxazoles have the most significant positive influence on the reactivity of the central iodine atom. A further catalyst improvement which focused on the substitution pattern of the arene revealed a remarkable ortho-effect. By introduction of an o-OMe group we were able to generate a novel NHIA with a so far unseen catalytic efficiency. This new catalyst is not only easy to synthesize but also enabled the α-tosyloxylation of carbonyl compounds at the lowest reported catalyst loading of only 1 mol%. Finally, the performance of this iodine(I) catalyst was successfully demonstrated in intramolecular oxidative couplings of biphenyls and oxidative rearrangements. (Figure presented.).

Intramolecular Homolytic Substitution Enabled by Photoredox Catalysis: Sulfur, Phosphorus, and Silicon Heterocycle Synthesis from Aryl Halides

Aryl radical generation and manipulation constitutes a long-standing challenge in organic synthesis. Photocatalytic single-electron reduction of aryl halides has been established as a premier activation pathway to reach these intermediates. The current st

Synthesis of Functionalized Alkylidene Indanes and Indanones through Tandem Phosphine-Palladium Catalysis

Densely functionalized alkylidene indanes and indanones can be prepared efficiently in one pot, in high yields with good stereoselectivities (in some cases exclusively the Z-isomer), through a route involving phosphine-catalyzed Michael addition followed

Palladium-catalyzed insertion of N-tosylhydrazones for the synthesis of isoindolines

Isoindolines are synthesized by palladium-catalyzed coupling reaction of N-(2-iodobenzyl) anilines with α,β-unsaturated N-tosylhydrazones. The reaction has several potential advantages: (1) toleration of a wide range of functional groups, (2) easy to handle and with mild conditions, (3) enriches the isoindoline family, (4) two new bonds form in one step.

New chiral iodooxazoline catalysts for the I(III)-mediated α-tosyloxylation of ketones: Refining the stereoinduction model

A new family of iodooxazoline catalysts, derived from widely available chiral ketones (menthone and camphor), was developed to promote the iodine(III)-mediated α-tosyloxylation of ketone derivatives. The reaction conditions to achieve the direct formation

Catalytic enantioselective α-tosyloxylation of ketones using iodoaryloxazoline catalysts: Insights on the stereoinduction process

A family of iodooxazoline catalysts was developed to promote the iodine(III)-mediated α-tosyloxylation of ketone derivatives. The α-tosyloxy ketones produced are polyvalent chiral synthons. Through this study, we have unearthed a unique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to the oxazoline oxygen atom is significant. Computational chemistry was used to rationalize the stereoinduction process. The catalysts presented promote currently among the best levels of activity and selectivity for this transformation. Evaluation of the scope of the reaction is presented.