107616-61-5Relevant academic research and scientific papers
Photo-induced Carboiodination: A Simple Way to Synthesize Functionalized Dihydrobenzofurans and Indolines
Yang, Xiaobo,Liu, Wenbo,Li, Lu,Wei, Wei,Li, Chao-Jun
supporting information, p. 15252 - 15256 (2016/10/13)
Herein, we report a simple, redox-neutral and pH-neutral photo-induced carboiodination reaction under very mild conditions. This protocol employs readily available and cheap aryl bromides and sodium iodide as the starting materials to synthesize valuable functionalized dihydrobenzofurans and indolines in good to excellent yields with broad functional-group compatibility. As examples to demonstrate the utility of this protocol, gram-scale reactions and further transformations of the products were accomplished towards the synthesis of bioactive drug candidates. Most significantly, to the best of our knowledge, this reaction represents the first example of a cascade atom-radical-transfer addition involving the cleavage of aromatic C?Br bond.
Cyclizing radical carboiodination, carbotelluration, and carboaminoxylation of aryl amines
Hartmann, Marcel,Studer, Armido
, p. 8180 - 8183 (2014/08/18)
Radical carboiodination of various aryl amines is reported. Aryl diazonium salts, generated in situ from the corresponding aryl amines, are reacted with Bu4NI to provide the corresponding aryl radicals which undergo 5-exo or 6-exo cyclization. Iodine abstraction eventually affords the carboiodinated products in good to excellent yields. If TEMPO is added, the cascade provides the cyclized carboaminoxylation products. Running the reaction in the presence of PhTeTePh affords the phenyltellurated cyclized products.
Diastereoselective intramolecular SmI2-H2O-amine mediated couplings
Dahlen, Anders,Petersson, Annika,Hilmersson, Goeran
, p. 2423 - 2426 (2007/10/03)
The effectiveness of SmI2-H2O-amine mixture for intramolecular couplings was discussed. Diastereoselectivities in the coupling of O-cyclohexanyliodophenol derivatives were provided into heterocycles. The amount of coupled product improved significantly as SmI2, the substrate and amine were premixed followed by a gradual addition of water.
Iododediazoniation of Arenediazonium Salts Accompanied by Aryl Radical Ring Closure
Beckwith, Athelstan L. J.,Meijs, Gordon F.
, p. 1922 - 1930 (2007/10/02)
Treatment of o-(allyloxy)benzenediazonium tetrafluoroborate (1a) with sodium iodide in acetone affords the cyclized iodide 2a in good yield by a mechanism involving the generation and exo cyclization of the aryl radical 6a.Other diazonium salts (1b-i) containing suitable unsaturated side chains behave similarly, but those (1l,1m) in which there is an N-allylsulfonamido group yield mainly products formed by endo cyclization.The diazonium salts 1j and 1k do not give cyclized products.Factors affecting the mechanism, rates, and regiochemistry of the reaction are discussed.
