79069-32-2Relevant articles and documents
Perfluoroalkanesulfonylation of Alkynyl(phenyl)iodonium Tosylates by the Weakly Nucleophilic Sodium Perfluoroalkanesulfinates
Han, Jia-Bin,Yang, Lian,Chen, Xing,Zha, Gao-Feng,Zhang, Cheng-Pan
supporting information, p. 4119 - 4124 (2016/12/30)
An additive- and transition metal-free perfluoroalkanesulfonylation of alkynyl(phenyl)iodonium tosylates with sodium perfluoroalkanesulfinates (RfnSO2Na) is described. The poorly nucleophilic RfnSO2Na reacted with alkynyl(phenyl)iodonium salts in dichloromethane at room temperature under a nitrogen atmosphere for 5–60 minutes to afford a variety of acetylenic triflones and alkynyl perfluoroalkyl sulfones in good to quantitative yields. The position of substituents on the phenyl rings of the arylethynyl moiety in the iodonium salts had a big influence on the reaction. The formation of five-membered cyclic vinyl sulfones suggested that the reaction proceeds via an alkylidene carbene intermediate. Furthermore, successful scaling-up of the reaction demonstrates the practicality of the new method. Advantages of the method include short reaction times, mild conditions, and the easy access to perfluoroalkanesulfonylation reagents (RfnSO2Na). (Figure presented.).
Synthesis and reactivity of aryl(alkynyl)iodonium salts
Dixon, Luke I.,Carroll, Michael A.,Gregson, Thomas J.,Ellames, George J.,Harrington, Ross W.,Clegg, William
, p. 2334 - 2345 (2013/05/21)
The first practical, yet simple, preparation of aryl(alkynyl)iodonium trifluoroacetate salts is described. The generic nature of this synthetic method has allowed the production of a range of aryl(alkynyl)iodonium trifluoroacetate salts with independent variation of both the alkynyl and aryliodo groups in yields of 30-85 %. Application of these new reagents to the synthesis of a series of 2-arylfuro[3,2-c]pyridines (40-64 %) highlights the potential of this class of materials as precursors to bioactive heterocyclic structures. These experiments have also demonstrated that, in this case, the effect of the aryliodo group on the reaction is negligible.
Nucleophilic fluorination of alkynyliodonium salts by alkali metal fluorides: Access to fluorovinylic compounds
Nguyen, Thi-Huu,Abarbri, Mohamed,Guilloteau, Denis,Mavel, Sylvie,Emond, Patrick
body text, p. 3434 - 3439 (2011/06/19)
Fluorovinylic compounds were synthesized by a one-pot procedure from the corresponding alkynyliodonium salts and alkali metal fluorides. Different reaction parameters, such as the temperature, the solvent and the reaction time were examined, and interesti
Reactivity of Arylethynyl(phenyl)iodonium Salts Towards some 1,3-Dipoles. X-Ray Molecular Structure of 3-Mesityl-5-phenylisoxazol-4-yl(phenyl)iodonium Toluene-p-sulphonate
Kotali, Elvira,Varvoglis, Anastassios,Bozopoulos, Anastassios
, p. 827 - 832 (2007/10/02)
Three arylethynyl(phenyl)iodonium salts reacted as 1,3-dipolarophiles with two nitrile oxides to afford phenyl(substituted isoxazolyl)iodonium salts; these gave iodoisoxazoles on reaction with nucleophiles.Phenyl(phenylethynyl)iodonium toluene-p-sulphonate reacted in the same way with nitrones but the resulting phenyl(substituted isoxazolinyl)iodonium salts, with one exeption, were difficult to isolate because of ready hydrolysis.The crystal structure of 3-mesityl-5-phenylisoxazol-4-yl(phenyl)iodonium toluene-p-sulphonate has been determined.
Exchange of Carbon Ligands at Iodine in Iodonium Salts. A Direct Synthesis of Aryl(2-furyl)iodonium Tosylates from Aryl(tert-butylethynyl)iodonium Tosylates
Margida, Anthony J.,Koser, Gerald F.
, p. 4703 - 4706 (2007/10/02)
Various arenes (RC6H4I(OH)OTs, R=H, 2-Me, 3-Me, 4-Me,2-F, 3-F, 4-F, 2-Cl, 3-Cl) have been found to react with tert-butylacetylene in chloroform under reflux to give the corresponding aryl-(tert-butylethynyl)iodonium tosylates formu
Alkynylaryliodonium Tosylates and Aryliodonium Tosylates from Reactions of Terminal Alkynes with benzene
Rebrovic, Louis,Koser, Gerald F.
, p. 4700 - 4702 (2007/10/02)
Various terminal alkynes have found to react with benzene (4) in CHCl3 to give either aryliodonium tosylates 5 or alkynylaryliodonium tosylates 6 or a mixture of the two.The product composition is subject to steri
Functionalization of Alkenes and Alkynes with benzene. Bis(tosyloxy)alkanes, Vinylaryliodonium Tosylates, and Alkynylaryliodonium Tosylates
Koser, Gerald F.,Rebrovic, Louis,Wettach, Richard H.
, p. 4324 - 4326 (2007/10/02)
benzene (1) reacts with various alkenes to give bis(tosyloxy)alkanes and with various alkynes to give either vinylaryliodoniumtosylates or alkynylaryliodonium tosylates.In the presence of 1, 1,1-diphenylethylene undergoes oxidative rearrangement and phenyliodination.
