Iron-catalyzed Cross-Coupling Reactions

People

Faculty
  Marc Perry

Student Researchers
  Jessica Lazar

Abstract

The ability to form C-C bonds is of paramount importance in organic synthesis. Currently, some of the best synthetic methods for forming C-C bonds use transition metal catalysts. The catalysts most often used employ palladium which is expensive, and has some limitations in the substrate scope. In all of the cross-coupling reactions catalyzed by palladium aryl chlorides are the least reactive of the aryl halides. However, aryl chlorides are more readily available, less expensive, and more stable than the corresponding aryl bromides or iodides, and the development of methods for the use of aryl chlorides in cross coupling reactions would prove very valuable. We are building on some preliminary work done by others which employs iron as a catalyst in the coupling of alkyl Grignards and aryl chlorides. N-heterocyclic carbenes will be employed as ligands in hopes of stabilizing the low valent iron species produced when treated with alkyl Grignard reagents. This should allow for the use of coupling partners other than alkyl Grignards in the cross-coupling reaction with aryl chlorides. Specifically, terminal alkynes will be used in a reaction in a Sonogashira coupling and 1,3-dicarbonyls will be used in a a-arylation reaction. If these reactions are found to proceed as proposed, then the iron carbene catalysts used would prove to be suitable substitutes for palladium-based catalysts. This would make the use of these powerful C-C bond-forming reactions more economically viable for industrial applications.

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