Amberlite IRA900F as a Solid Fluoride Source for a Variety of Organic Transformations under Solvent‐Free Conditions

Abstract

We have reported that Amberlite IRA900F (Amb-F) is an efficient metal-free catalyst for the activation of Si-N and Si-O bonds and a mild base in a variety of organic transformations under solvent-free conditions, such as the addition of TMSN 3 to (E)-2-aryl-1-cyano-1-nitroethenes, nitriles, α,β-unsaturated

Synthesis of β‐Cyano Ketones Promoted by a Heterogeneous Fluoride Catalyst

“…The efficiency of the different solid fluoride sources strongly depends on the counter ion, especially if polymer‐supported, that has an influence on the availability and nucleophilicity of the fluoride ion towards silicon atom. This is not surprising, also on the basis of our previous experience on the influence of the solid polymeric support on the efficiency of an immobilized catalyst 12,15,17,19,20,22. A striking example is given by the different efficiency showed by Amberlite ® IRA 400F (a gel‐type polystyrene resin) and Amberlite ® IRA 900F (a macroreticular polystyrene resin) (Table 1, entry 2 vs. 6).…”

“…In recent years, we have focused our attention on processes proceeding via fluoride activation of silicon pronucleophiles12 in various types of addition reactions. A few examples are the Mukaiyama aldol reaction13 catalyzed by Amberlite ® IRA 900F (Amb‐F), a commercially available tetramethylammonium fluoride salt supported on a porous type polystyrene,14 the β‐azidation of α,β‐unsaturated ketones catalyzed by PS‐DABCOF 2 ,15 a bis‐ammonium fluoride salt of 1,4‐diazabicyclo[2.2.2]octane supported on gel type polystyrene resin,16 and the β‐azidation of carboxylic acids catalyzed by PS‐DABCOF,17 the mono‐ammonium fluoride derivative of 1,4‐diazabicyclo[2.2.2]octane supported on a gel type polystyrene.…”

Chemistry of 2-aryl-1-cyano-1-nitroethenes. Part II. Chemical transformations

“…These reagents subsequently experienced aromatization and [1.3]-sigmatropic hydrogen shift, leading to 4-aryl-1H-1,2,3-triazole-5-carbonitriles (15a-g) with excellent yield (Table 3). [14]. The catalysed process was the reaction between (E)-ACNs (1, 16a-e) and azido(trimethyl)silane (13) carried out in the presence of Amberlite IRA900F (Amb-F).…”

Aryl(hetaryl)-containing gem-cyanonitroethenes: Synthesis, structure, and reactions with 2,3-dimethyl-1,3-butadiene

“…Their reactions with 1,3-dipoles [7,[38][39][40][41][42] and vinyl ethers [43][44][45] yielding practically important cyclic compounds are of the particular interest.…”