Potassium fluoride on calcium fluoride – a practical reagent for removal of organotin residues from reaction mixtures

Methodologies Limiting or Avoiding Contamination by Organotin Residues in Organic Synthesis

“…In addition to the efficiency of the purification, the K 2 CO 3 /silica stationary phase is cheap and stable over several months. More recently, Pivnitsky et al reported the use of a mixture of fluorous salts (KF/CaF 2 , 20 wt % of KF) to easily remove tributyltin derivatives by filtration on a plug of silica after conversion into Bu 3 SnF …”

“…More recently, (KF/CaF 2 , 20 wt % of KF) to easily remove tributyltin derivatives by filtration on a plug of silica after conversion into Bu 3 SnF. 92…”

Scalable Sn-Catalyzed Regioselective Allylation of 1-Methyl-l-α-rhamnopyranoside

“…While column chromatographic purification successfully afforded the desired product in 82% yield with nondetectable residual Sn on a 50 g scale reaction, it is desirable to develop a scalable isolation/purification process that circumvents the need for column chromatographic purification on large scale. Over the years many research groups have reported methods for the removal of residual organotin; − however, most of them still require the use of column chromatographic purification. During our research we opted to take advantage of the solubility difference between the desired product and other components, including organotin species, in the reaction matrix.…”

Stille polycondensation: a multifaceted approach towards the synthesis of polymers with semiconducting properties

“…Organotin compounds can also be readily converted into insoluble polymeric fluorides through filtration with a potassium fluoride-celite mixture. 114 Further alternative methods include treatment with DBU and water, 115 oxidation and formation of SnS 2 , 116 and other modifications, 117,118 which not only reduce the toxicity of chemical waste but can also be used in high-scale operations at relatively low cost. Despite the challenges associated with toxicity of tin compounds, the Stille polycondensation remains a frequently employed method owing to the availability of effective ways to address the toxicity issues.…”

“…Organotin compounds can also be readily converted into insoluble polymeric fluorides through filtration with a potassium fluoride–celite mixture. 114…”