220966-24-5Relevant academic research and scientific papers
Multimetallic iridium-tin (Ir-Sn3) catalyst in N-acyliminium ion chemistry: Synthesis of 3-substituted isoindolinones via intra- and intermolecular amidoalkylation reaction
Maity, Arnab Kumar,Roy, Sujit
, p. 2627 - 2642 (2014/09/30)
The multimetallic iridium-tritin (Ir-Sn3) complex [Cp*Ir(SnCl3)2{SnCl2(H2O) 2}] (1) proved to be a highly effective catalyst towards C-OH bond activation of γ-hydroxylactams, leading to a nucleophilic substitution reaction known as the α-amidoalkylation reaction. Catalyst 1 can be easily synthesized from the reaction of (pentamethylcyclocyclopentadienyl)iridium dichloride dimer {[Cp*IrCl2]2} and tin(II) dichloride (SnCl2). In terms of catalyst loading, reaction conditions and yields of the product formed, 1 is found to be superior compared to classical Lewis acid catalysts. Different carbon (arenes, heteroarenes, allyltrimethylsilane, 1,3-dicarbonyls) and heteroatom (alcohols, thiols, amides and sulfonamides) nucleophiles have been successfully employed in the intramolecular and intermolecular alkylations, as well as in heterocyclization reactions. In the majority of cases good to excellent yields of 3-substituted isoindolinones and 5-substituted pyrrolidin-2-ones have been obtained. Besides, the reactions are also atom economical and salt free. It is proposed that the multimetallic Ir-Sn3 catalyst behaves as a mild and selective Lewis acid to activate the γ-hydroxylactam towards the formation of the N-acyliminium ion; the latter being trapped by potent nucleophiles leading to the desired products.
Intermolecular and intramolecular α-amidoalkylation reactions using bismuth triflate as the catalyst
Pin, Frederic,Comesse, Sebastien,Garrigues, Bernard,Marchalin, Stefan,Daich, Adam
, p. 1181 - 1191 (2007/10/03)
(Chemical Equation Presented) Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The α-amidoalkylation process seems to be effective in intermolecular and intramolecul
Synthesis of isoindolo[1,3]benzoxazine derivatives through intramolecular arylation of N-acyliminium ions
Hucher, Nicolas,Daich, Adam,Decroix, Bernard
, p. 1477 - 1483 (2007/10/03)
[1,3]Benzoxazines annulated to isoindole as 3 and 4 have been synthesized in three steps from N-chloromethylphthalimide 5 and substituted phenols 6. The key step was the acid-catalyzed cyclization of ω-carbinol lactams 8 and 9.
