10075-72-6Relevant articles and documents
Combined Experimental and Theoretical Studies on the Radical Nucleophile Addition Reaction for Sulfide- and Selenide-Centered Anions
Bouchet, Lydia M.,Pe?é?ory, Alicia B.,Pierini, Adriana B.,Argüello, Juan E.
, p. 5035 - 5042 (2019)
The reactivity of sulfur- and selenium-centered nucleophiles toward 1-naphthyl radicals was studied in dimethylsulfoxide. The photostimulated reaction of sulfide anions, -SC(NH)C6H5 (1), -SC(NH)NH2 (2), and -SC(NH)CH3 (3), renders, after the addition of MeI, methyl 1-naphthylsulfide as a main product together with bis(1-naphthyl) sulfide and naphthalene under irradiation. Concordantly, the reaction of selenide anions, -SeC(NH)C6H5 (4), -SeC(NH)NH2 (5), and -SeCN (6), produces methyl 1-naphthyl selenide, bis(1-naphthyl) selenide, and naphthalene in the presence of potassium tert-butoxide anion (entrainment conditions). Absolute rate constants for the coupling of ions 1-6 to 1-naphthyl radicals were determined; as a general trend, the selenide-centered nucleophiles enhance in 2 times the reactivity of their sulfide analogues. From the mechanistic study, it is proposed that the unstable radical anion produced by the addition of the nucleophile to 1-naphthyl radical affords, after fragmentation, 1-naphthylsulfide/selenide anion. In addition, experimental results are discussed in terms of density functional theory calculations. There is a generally good agreement between the experimental and the calculated reactivities, the spin density being the main parameter to describe the difference found among the anions under study. Moreover, the calculations predict that anion -SeC(NH)CH3 (7) would be a good candidate for the synthesis of selenide derivatives.
POLYFLUOROALKYLATION OF BROMOAROMATIC COMPOUNDS VIA PERFLUOROALKYLCOPPER INTERMEDIATES
Chen, Grace J.,Tamborski, Christ
, p. 207 - 228 (1989)
Cross coupling reactions between various perfluoroalkyl iodides, copper and mono and dibromobenzenes, as well as mono and dibromobenzenes containing functional groups e.g., OH, CO2H, CO2R, NO2, NH2, OCH3 and C(O)CH3 have produced perfluoroalkyl substituted aromatic compounds in good to excellent yields.From certain bromo arenes, by-products were obtained, indicating competing reactions.These reactions may be due to the slower rate of cross coupling between a carbon-bromine bond and the perfluoroalkylcopper intermediate as compared to the cross coupling reaction involving a carbon-iodine bond with the perfluoroalkylcopper intermediate.
Organocatalytic visible light mediated synthesis of aryl sulfides
Majek, Michal,Von Wangelin, Axel Jacobi
supporting information, p. 5507 - 5509 (2013/06/27)
Photo-sensitized synthesis of arylsulfides from arenediazonium salts in the presence of eosin Y has been developed. This protocol exhibits high functional group tolerance and a wide substrate scope and is an attractive alternative to the thermal reaction that involves explosive intermediates.
