107616-15-9Relevant academic research and scientific papers
Twofold carbon-carbon bond formation by intra- and intermolecular radical reactions of aryl diazonium salts
Jasch, Hannelore,Landais, Yannick,Heinrich, Markus R.
, p. 8411 - 8416 (2013)
Cascade reactions: A variety of novel cascade reactions can be performed when the known and well-studied radical 5- or 6-exo-cyclization of an aryl diazonium salt is conducted in the presence of alkenes and further optional scavengers (see scheme). Copyri
Enantioselective Aza-Wacker-Type Cyclization Promoted by Pd-SPRIX Catalyst
Sen, Abhijit,Takenaka, Kazuhiro,Sasai, Hiroaki
supporting information, p. 6827 - 6831 (2018/11/02)
An enantioselective aza-Wacker-type reaction was developed. When alkenyl sulfonamide substrates were treated with the Pd-SPRIX catalyst in the presence of oxone as an oxidant, the olefin was attacked intramolecularly by the nitrogen nucleophile to constru
Copper-catalyzed carbochlorination or carbobromination via radical cyclization of aryl amines
Ouyang, Jianing,Su, Xiaolong,Chen, Yu,Yuan, Yaofeng,Li, Yi
supporting information, p. 1438 - 1441 (2016/03/12)
A copper-catalyzed radical carbochlorination or carbobromination is reported. Intramolecular cyclization occurred through aryl radicals generated in situ from bench-stable aryl amines with aqueous hydrogen halides as the halogen sources. A variety of (3-h
Cyclizing radical carboiodination, carbotelluration, and carboaminoxylation of aryl amines
Hartmann, Marcel,Studer, Armido
supporting information, 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.
Tetrathiafulvalene: a catalyst for sequential radical-polar reactions
Fletcher, Rodney J.,Lampard, Christopher,Murphy, John A.,Lewis, Norman
, p. 623 - 634 (2007/10/02)
The reaction between tetrathiafulvalene (TTF) and suitable arenediazonium salts leads to products arising from an ordered sequence of reactions featuring electron transfer, loss of nitrogen, radical cyclisation and nucleophilic substitution.The tetrathiafulvalenium salt 6 is shown to be an intermediate in the reaction, with substitution of TTF occuring via an SN1 mechanism.The reactions are catalytic in TTF and the final substitution can be achieved by several nucleophiles.Extension of the reaction to the synthesis of bi- and tricyclic ring systems has been investigated.
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.
