90786-22-4Relevant academic research and scientific papers
Mono- vs. dinuclear gold-catalyzed intermolecular hydroamidation
Serrano-Becerra, Juan M.,Maier, Alexander F. G.,Gonzalez-Gallardo, Sandra,Moos, Eric,Kaub, Christoph,Gaffga, Maximilian,Niedner-Schatteburg, Gereon,Roesky, Peter W.,Breher, Frank,Paradies, Jan
, p. 4515 - 4522 (2014/08/05)
Mono- and dinuclear gold catalysts were investigated in the intermolecular hydroamidation of olefins. Upon activation of [Ph3PAuCl] and [xantphos(AuCl)2] with various silver salts (AgOTf, Ag[BF 4], and Ag[SbF6]), diverging reactivity of the resulting cationic gold complexes was observed. It was found that both the binding ability of the counterion and the solvent have a significant impact on the reactivity of the mono- and dinuclear complexes. Copyright
Gold versus silver-catalyzed intermolecular hydroaminations of alkenes and dienes
Giner, Xavier,Najera, Carmen,Kovacs, Gabor,Lledos, Agusti,Ujaque, Gregori
experimental part, p. 3451 - 3466 (2012/02/04)
Comparative studies about the hydroamination of unactivated alkenes and dienes catalyzed by either cationic gold(I) triphenyl phosphite complexes or silver salts were performed using sulfonamides, anilines and carbamates as nucleophiles. Gold-catalyzed reactions generally, need lower loadings than those carried out with silver salts. Simple alkenes react only with sulfonamides and weak aromatic amines such as p-nitroaniline, whereas for conjugated dienes carbamates can also be used. Carbon-carbon double bond isomerization is observed only with gold similarly to when triflic acid was used, affording mixtures of regioisomeric products in the same cases. Silver-catalyzed hydroaminations failed with terminal alkenes, except with styrenes. Conjugate dienes can be hydroaminated either at 85 °C in toluene or at room temperature in dichloromethane. Non-conjugated 1,4- and 1,5-dienes suffer double hydroamination leading to saturated N-tosylated heterocyclic amines The catalytic cycle for the silver(I)-catalyzed hydroamination process has been computationally analyzed, resembling gold(I)-catalyzed processes, although with some significant differences. Copyright
Sulphonamidomercuriation of Olefins and Subsequent Reductive Demercuriation or Bromodemercuriation
Barluenga, Jose,Jimenez, Carmen,Najera, Carmen,Yus, Miguel
, p. 721 - 725 (2007/10/02)
The addition of toluene-p-sulphonamide to olefins in the presence of anhydrous mercury(II) nitrate and subsequent sodium borohydride reduction leads to the corresponding N-alkylsulphonamides.The sulphonamidomercuriation-demercuriation of 1,4- and 1,5-dienes yields saturated nitrogen-containing heterocycles.A possible mechanism for the stereoselective synthesis of cis-2,5-dimethyl-N-tosylpyrrolidine is proposed.The treatment of the intermediate organomercurials, isolated as the sodium salts of their bromomercurio derivatives, with bromine gives the corresponding 2-bromoalkylsulphonamides through a regiospecific bromodemercuriation process.
