Allylations scandium trifluoromethanesulfonate

Allylations, allenylations, and propargylations of carbonyl compounds in aqueous media can also be carried out with preformed organic tin reagent, rather than the use of metals.86,87,88 For example, the allylation reaction of a wide variety of carbonyl compounds with tetraal-lyltin was successfully carried out in aqueous media by using scandium trifluoromethanesulfonate (scandium triflate) as a catalyst (Eq. 8.40).89 A phase-transfer catalyst (PTC) was found to help the allylation mediated by tin at room temperature without any other assistance.90... 

Hachiya, 1. and Kobayashi, S., Aqueous reactions with a Lewis acid and an organometalhc reagent. The scandium trifluoromethanesulfonate-catalyzed allylation reaction of carbonyl compounds with tetraallyltin, /. Org. Chem., 1993, 58, 6958-6960. 

For example, Kitazume and Zulfiqar have investigated the scandium(III) trifluorometh-anesulfonate catalyzed Claisen rearrangement of several aromatic allyl ethers in a neutral trifluoromethanesulfonate ionic liquids [45]. The reaction initially gave the 2-allylphenol but this reacted further to give 2-methyl-2,3-dihydrobenzo[b]furan (Scheme 2). The yields in this reaction were highly dependant on the ionic liquid chosen, with [EDBU][OTf ] giving the best yields (e.g. 91% for R = 6-CH3). 

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