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DOI: 10.1055/s-0030-1260757
SnCl2/KI-Mediated Allylation Reactions of Formaldehyde in Water
Publication History
Publication Date:
21 June 2011 (online)
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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.
Key words
SnCl2/KI-mediated allylation reactions - aqueous solution - formaldehyde - homoallylic alcohols - 2-halohomoallylic alcohols
- Supporting Information for this article is available online:
- Supporting Information
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References and Notes
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.