Journal
SYNLETT
Volume 29, Issue 17, Pages 2316-2320Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1610657
Keywords
hypervalent iodine; iodobenzamide; organic catalysis; oxidative cleavage; Oxone ((R))
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[4-Iodo-3-(isopropylcarbamoyl)phenoxy]acetic acid was developed as a highly reactive and easily separable catalyst for the oxidative cleavage of tetrahydrofuran-2-methanols to -lactones in the presence of Oxone((R)) (2KHSO(5)center dot KHSO4 center dot K2SO4) as the co-oxidant. The reactivity of this new catalyst was considerably greater than that of our previously reported catalyst, 2-iodo-N -isopropylbenzamide. The new catalyst and product were easily separated by only liquid-liquid separation without chromatography. In addition, using a mixture of nitromethane and N,N-dimethylformamide as the solvent and heating enabled a low catalyst loading, a short reaction time, and high product yield. Oxidative cleavage using the new catalyst can be used as a practical and efficient method for synthesizing gamma-lactones.
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