Ionic Liquid Supported Organotin Reagents: Green Tools for Stille Cross‐Coupling Reactions with Brominated Substrates

Abstract

Efficiency of ionic liquid supported organotin reagents in Stille cross‐coupling reactions involving aryl bromides has been investigated. In a general manner, products were isolated with good yields by using a very simple catalytic system without the need of solvent, ligand, or additives. The organotin compounds were recycled without loss of activity and the contamination by tin was limited and controlled ([Sn] < 3 ppm).

Heterocycles-Based Ionic Liquid-Supported Synthesis of Small Organic Molecules

“…Legoupy and coworkers have reported the synthesis of novel IL-supported organotin reagents 167, which were successfully used in Stille cross-coupling reactions (Scheme 21) [61,62]. Notably, these transformations were performed without solvents, ligands, and additives, and just by using commercially available precatalysts.…”

Safer and Greener Catalysts – Design of High Performance, Biodegradable and Low Toxicity Ionic Liquids

“…Legoupy and co-workers reported an ionic liquid supported organotin reagent which can recycled and minimise contamination of product by organotin compound, without the use of solvent and additives. [65] Ionic liquids supported dibutylphenyltin was successfully synthesized and used as a reagent in palladium catalyzed Stille cross-coupling reactions involving brominated substrates under solvent-free conditions. An effective use of different ionic liquid supported vinyl, allyl, aryl and heteroaryl organotin reagents with aryl bromides have seen use in Stille cross-coupling reaction.…”

Nanocatalysts for Hiyama, Stille, Kumada, and Negishi C–C Coupling Reactions

“…Recent experiments, however, suggest that hydrophobic ILs, supercritical carbon dioxide, or highly polar sugar/urea/salt melts may also serve as good reaction media for Stille coupling. [123][124][125] While Pd with or without ligands has traditionally been used as a catalyst, contemporary literature is also rich in examples where CuI, ZnCl 2 , LiCl, MnBr 2 , and so on, have been used as catalysts and/or cocatalysts/additives to enhance the yields and improve product selectivities. 23 Other modifications include the use of N,N-diisopropylethylamine, or Hünig's base and silica-bound cysteine, the latter a tin scavenger.…”