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Communication | Special issue | Vol 90, No. 1, 2015, pp.144-149
Published online, 16th July, 2014
DOI: 10.3987/COM-14-S(K)45
Palladium(0)-Mediated C−S and O−H Bonds Cleavage Reaction in 2-Hydroxybenzyl Phenyl Sulfide: Formations of Oxyphosphorane and 1,2-Oxapalladacycle

Norio Nakata, Noriyuki Furukawa, Hiroki Kobayashi, Izuru Suzuki, and Akihiko Ishii*

*Department of Chemistry, Faculty of Science, Saitama University, Urawa, Saitama 338-8570, Japan


Treatment of 2-hydroxybenzyl phenyl sulfide 3 with 1.5 equiv. of [Pd(PPh3)4] in toluene led to the unanticipated formation of oxyphosphorane 4 in 30% isolated yield. In contrast, the reaction of 3 with Pd(0) complex bearing PMe3 ligands in toluene afforded the corresponding 1,2-oxapalladacycle 7 and oxyphosphorane 9 in addition to dithiolato complex trans-[Pd(SPh)2(PMe3)2] 8.