Reaction of 1-bromonaphthalene with PH 3 in the t -BuOK/DMSO system: PCl 3 -free synthesis of di(1-naphthyl)phosphine and its oxide

Abstract 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.