1293024-74-4Relevant academic research and scientific papers
Gold(III)/Sodium Diphenylphosphinobenzene-3-sulfonate (TPPMS) Catalyzed Dehydrative N-Benzylation of Electron-Deficient Anilines in Water
Azumaya, Isao,Hikawa, Hidemasa,Kikkawa, Shoko,Matsumoto, Mika,Tawara, Sayoko
, p. 2729 - 2736 (2019)
A strategy for the dehydrative N-benzylation of electron-deficient anilines in water has been developed. The gold(III)/sodium diphenylphosphinobenzene-3-sulfonate (TPPMS) catalyst is highly effective as a Lewis acid for the activation of alcohols and tolerates aerobic conditions. A Hammett study in the reaction of para -substituted benzhydryl alcohols shows negative σ values, indicating a build-up of cationic charge during the rate-determining sp 3 C-O bond-cleavage step. The inverse kinetic solvent isotope effect (KSIE = 0.6) is consistent with a specific acid catalysis mechanism. This simple protocol can be performed under mild conditions in an atom-economic process without the need for base or other additives, furnishing the electron-deficient N -benzylic anilines in moderate to excellent yields along with water as a sole coproduct.
Iron-catalyzed C-C bond cleavage and C-N bond formation
Li, Wenjuan,Zheng, Xiaojian,Li, Zhiping
, p. 181 - 190 (2013/03/13)
A novel approach for C-N bond formation was developed by iron-catalyzed C-C bond cleavage. Anilines and sulfonamides reacted smoothly with 2-substituted 1,3-diphenylpropane-1,3-diones to afford N-alkylation products, in which the 1,3-dicarbonyl group acts as a leaving group in the presence of an iron catalyst. The reversible C-C bond cleavage plays a driving force to give the thermodynamically stable products. The method is complementary to the previous methods for C-N bond formation. Copyright
