Abstract
Even if water is the natural environment for bioorganic reactions, its use in organic chemistry is often severely limited by the high insolubility of the organic derivatives. In this review, we introduce some examples of the use of water to perform organoselenium chemistry. We mainly discuss the advantages of this medium when the recyclability is demonstrated and when the water can control the selectivity of a reaction or enhance the reaction rate.
Highlights
During the last two decades, the use of water as an alternative solvent for organic reactions has been debated
Even if water is commonly used as a reactant reactant for for the the electrophilic electrophilic hydroxyselenenylation hydroxyselenenylation of double and triple bonds [14], to the best of our knowledge the first examples reporting its use as medium referred to the formation and the reaction of nucleophilic species of selenium mediated by metals
The authors reported combination of water withantimony, different organic mechanism proposed by the authors, produces a benzylantimony intermediate by the reaction with as EtOH, DMF, and THF, proving that in a 3:1 mixture of THF and H2O the reaction is considerably benzyl bromide and reacts with the diselenide, even if, in our opinion, a direct oxidative insertion faster, giving up to 85% yield in 8 h compared to the 12 h required for other aqueous media [19] and
Summary
During the last two decades, the use of water as an alternative solvent for organic reactions has been debated. Breslow [3], Sharpless [4], and several other authors [5] reported reactions that can be efficiently conducted “in-water” or “on-water” conditions This latter term describes those reactions that when performed in vigorously stirred aqueous suspension showed a remarkable rate acceleration, only partially due to the well-known hydrophobic effect [6], which, on the contrary, has been demonstrated to be responsible for the selectivity observed in some biomimetic protocol performed using water as a reaction medium [7,8,9,10,11]. The result is that in those cases the water recovered as waste is contaminated by toxic elements, representing a limitation for its use as a green alternative solvent [12]. The data reported in literature but a selection of examples that clarify our ideas on the topic
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