(28) Organometallic Iron Catalysts for Amide Synthesis

     Amides are widely used in many regions of production including the pharmaceutical and polymer industries. Currently, however, the means of synthetically creating amides through traditional organic methods are... [ view full abstract ]

     Amides are widely used in many regions of production including the pharmaceutical and polymer industries. Currently, however, the means of synthetically creating amides through traditional organic methods are considered to be wasteful, toxic, and difficult to optimize for a wide variety of reagents. Alternatively, Ru^II centered organometallic catalysts to produce amides can be used to reduce waste and make more versatile amide derivatives via a single synthetic procedure. In order to reduce the cost associated with mid-transition metals, we substituted the Ru^II center for a Fe^II center. The precatalyst, (h⁶-arene)Fe^II(Cl)(^tbpy), was generated by first synthesizing (^tbpy)Fe^IICl₂ (^tbpy = tert-butyl-2,2′-dipyridyl) from Fe^IICl₂ and ^tbpy in a toluene solution followed by the addition of an h⁶-arene. The catalytic activity of this Fe^II catalyst was examined through the intramolecular dehydrogenation reaction of 1,4-butanediol to yield butyrolactone and intramolecular dehydrogenative amide formation of N-butylvalerolactam from N-butyl-5-amino-1-pentanol.