PBr3-mediated unexpected reductive deoxygenation of α-aryl-pyridinemethanols: synthesis of arylmethylpyridines

Abstract PBr3-mediated reductive deoxygenation of α-aryl-pyridinemethanols to provide arylmethylpyridines is described, the alcohol substrate scope is explored, free radical trap TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) is introduced, and the hydrogen source of the methylene product is defined. The unexpected reaction enabled us to prepare previously inaccessible, novel EP1 antagonists.