Reaction of 1-bromonaphthalene with PH3 in the t-BuOK/DMSO system: PCl3-free synthesis of di(1-naphthyl)phosphine and its oxide

Add time:08/18/2019    Source:sciencedirect.com

The phosphine, generated together with hydrogen from red phosphorus and aqueous KOH, reacts with 1-bromonaphthalene in the t-BuOK/DMSO system under mild conditions (70 °C, atmospheric pressure) to give di(1-naphthyl)phosphine, which is easily oxidized in the presence of air to afford di(1-naphthyl)phosphine oxide in 45% preparative yield. Tri(1-naphthyl)phosphine and naphthalene are also formed in the reaction in 23 and 27% yield, respectively. According to ESR and UV data, the studied phosphination of 1-bromonaphthalene involves a single electron transfer process.

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