SnCl₂/KI-Mediated Allylation Reactions of Formaldehyde in Water

Abstract

An efficient procedure for SnCl₂/KI-mediated allylation reactions of formaldehyde with a variety of allylic bromides in aqueous solution is reported. Under conditions developed in this effort, various homoallylic alcohols and 2-halohomoallylic alcohols are produced in good to excellent yields.

SnCl₂/KI-mediated allylation reactions - aqueous solution - formaldehyde - homoallylic alcohols - 2-halohomoallylic alcohols

References and Notes

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General Procedure for SnCl₂/KI-Mediated Allylation Reactions of Formaldehyde
A mixture of formaldehyde (82 mg, 1.0 mmol, 37 wt% aq solution), the allylating agent 2 (1.5 mmol), tin chloride dihydrate (339 mg, 1.5 mmol), and KI (249 mg, 1.5 mmol) in H₂O (2 mL) was stirred at r.t. overnight. The mixture was extracted with CH₂Cl₂ (3 × 5 mL). The combined organic layers were dried over Na₂SO₄ and concentrated in vacuo. The residue was subjected to silica gel chromatography by using Et₂O-hexanes (1:9) as eluent to give the product 1.