Oxy-Wittig reactions of 1-naphthyl(aryl)methylphosphonates: a new approach to naphthylarylketones

Add time:08/04/2019    Source:sciencedirect.com

Valuable compounds, naphthylarylketones are synthesized via oxy-Wittig (oxygenation of phosphonate carbanions) type reactions of diverse 1-naphthyl(aryl)methylphosphonates at room temperature by producing water soluble by-product. Commercially known but synthetically unexposed and expensive naphthylarylketones are easily synthesized using this transition metal-free, operationally simple strategy. As precursors, a range of new naphthyl(aryl)methylphosphonates are obtained in excellent yield and regioselectivity by direct and clean synthetic protocol that involves FeCl3 or triflic acid (TfOH) mediated arylation reactions of easily accessible (hydroxy)-1-naphthylmethylphosphonate with activated as well as unactivated arenes including halogenated anisoles, biphenyl, naphthalene and pyrene (extended π-systems) at room temperature.

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