56751-80-5

Upstream product

• 57056-93-6 N-methyl-2-iodoaniline 
• 98-59-9 p-toluenesulfonyl chloride 
• 1221594-10-0 N-tert-butoxycarbonyl-2-iodo-N-methylaniline 
• 161117-84-6 tert-butyl 2-iodophenylcarbamate 
• 615-43-0 2-iodophenylamine 
• 61613-20-5 N-tosyl-2-iodoaniline 
• 74-88-4 methyl iodide 

Downstream Products

• 1192372-84-1 N-(2-iodylphenyl)-N,4-dimethylbenzenesulfonamide 
• 1011801-35-6 1-(N-methyl-N-tosyl)-5,6-dihydro-9-chloro-10-azaindolo[2,1-a]isoquinoline 

Relevant academic research and scientific papers

Acid-Promoted Expeditious Syntheses of Aminated Dibenzosultams via Palladium/Norbornene Cooperatively Catalysed C?H Amination/Arylation

Herein we reported a protocol to access aminated benzofused sultams through sequential ortho-amination, followed by ipso-arylation of aryl iodide bearing sulfonamide functional group via palladium/norbornene coorperative catalysis. This reaction has showcased a broad spectrum of substrate scope under mild conditions with moderate to good efficiency. (Figure presented.).

Aniline-Type Hypervalent Iodine(III) for Intramolecular Cyclization via C?H Bond Abstraction of Hydrocarbons Containing N- and O-Nucleophiles

We developed a method for the preparation of (diacetoxyiodo)-2-(N-alkylamido)benzene as an aniline-type hypervalent iodine(III). We also achieved direct cyclizations via C?H bond abstraction, such as the Hofmann-L?ffler-Freytag reaction, a direct amination, and a direct lactonization, using the aniline-type hypervalent iodine(III) to obtain corresponding products in high yields. (Figure presented.).

Synthesis of biaryls via intramolecular free radical ipso-substitution reactions

A variety of functionalised biaryls and heterobiaryls are prepared by intramolecular free radical [1,5]-ipso-substitution using sulfonamide and sulfonate derived tethering chains. The overall efficiency of the process is determined by appropriately positioned substituents on the aromatic acceptor ring. The extension of the process to benzylic sulfonates and their corresponding N-methylsulfonamide alternatives as substrates in potential [1,6]-ipso-substitution reactions leads mainly to the alternative [1,7] addition products.

Preparation, X-ray structure, and oxidative reactivity of N-(2-iodylphenyl)tosylamides and 2-iodylphenyl tosylate: Iodylarenes stabilized by ortho-substitution with a sulfonyl group

(Chemical Equation Presented) New tosyl derivatives of 2-iodylaniline and 2-iodylphenol were prepared by the dimethyldioxirane oxidation of the corresponding 2-iodophenyltosylamides or 2-iodophenyl tosylate and isolated as stable, microcrystalline products. Single-crystal X-ray diffraction analysis of N-(2-iodylphenyl)-N,4-dimethylbenzenesulfonamide revealed pseudocyclic structure formed by intramolecular I...O interactions between the hypervalent iodine center and the sulfonyl oxygens in the tosyl group. This tosylamide has an excellent solubility in organic solvents and is a potentially useful hypervalent iodine oxidant.

A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction

A norbornene-mediated palladium-catalyzed tandem alkylation/C-H functionalization sequence is described, in which an alkyl-aryl bond and a heteroaryl-aryl bond are formed in one pot. A variety of highly substituted six- and seven-membered ring annulated i

Palladium-catalyzed alkylation-hydride reduction sequence: Synthesis of meta-substituted arenes

(Chemical Equation Presented) A new three-component, palladium-catalyzed domino reaction which gives access to meta-substituted arenes using aryl iodides and primary alkyl halides is reported. Various functional groups are tolerated on both the aryl iodide and alkyl halide. In addition, isotopic labeling studies provide insight into the mechanism of this Catellani-type reaction.

Observations on the enforced orthogonality concept for the synthesis of fully hindered biaryls by a tin-free intramolecular radical ipso substitution

Hindered biaryls have been simply prepared using diazonium salt precursors and an intramolecular free radical [1,5] ipso substitution protocol. The introduction of an additional substituent ortho to the diazonium group in the σ aryl radical donor further enforces the formation of ipso substitution products and hence fully hindered biaryls are the favoured products.