RhIII Catalyzed Olefination of 2 Aryloxypyridines Using 2 Pyridyloxyl as the Removable Directing Group
An efficient RhIII catalyzed trans selective ortho olefination of 2 aryloxypyridines has been developed. The catalytic system is very effective for olefination of differently substituted 2 aryloxypyridines with acrylates, acrylamide and styrenes and exhibits broad compatibility with assorted olefinic coupling partners. Although acrylates and acrylamide give rise to trans olefinated products in MeOH, styrenes provided the trans products under solvent free reaction conditions. Interestingly, in olefinations with ethyl acrylate, the aryloxypyridine compound bearing keto functionality at the ortho position was found to undergo directing group cleavage to afford the olefinated phenol product directly.