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The Use of N-heterocyclic Carbenes in Iron Catalyzed Cross Coupling Reactions

Status Current
Seeking Researchers No
Start Date 07/01/2009
End Date 06/30/2010
Funding Source Undergraduate Research Grant
Funding Amount
Community Partner
Related Course
Last Updated 07/13/2009 11:30PM
Keywords iron catalyzed cross coupling reaction

People

Faculty
  Marc Perry

Student Researchers
  Sean Egan

Abstract

Scientists utilize various catalytic pathways to create carbon-carbon bonds. One of these pathways belongs to a group of reactions named iron catalyzed cross coupling reactions. In these reactions, iron bound to ligand is used to form new carbon-carbon bonds by the use of Grignard reagents. These pathways are very similar to those that are palladium, with the exception that they are cheap and less well studied. Because this pathway is catalytic, requires no energy input, and is stable under certain circumstances, it is more environmentally friendly than alternatives, and is recyclable. Because of its ecological implications and lower cost, development of this iron-catalyzed pathway should be studied further. Unfortunately, a suitable ligand has yet to be found which stabilizes this reactive iron (-II) ligand complex while maintaining or maximizing its reactive ability. Evidence suggests that N-Heterocyclic Carbenes, more specifically imidazol-2-ylidene and imidazolin-2-yilidene, could potentially stabilize this complex due to their suspected pi acidity, sigma donating abilities, and variability of their steric bulk. If these carbenes could stabilize the iron ligand complexes mentioned, their applicability would extend much farther than previously anticipated, and numerous industries would be able to reap the rewards of using a catalyst that is reusable, requires no heat input, and is inexpensive.

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