Low Temperature Coupling Reactions of Sensitive Organometal Nucleophiles

• Applicant: Dr. Marcel Alexander Düfert
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2011 to 2012
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 193393382

Modern organic chemistry, both in academia and industry, relies on a wide array of methods to achieve its respective synthetic goals. Several Nobel Prizes have been awarded to chemists and their work connected to the development of new methodologies. Thus, previously unattainable reactions on highly complex substrates have become accessible and continue to be used by todays chemical community. Especially transition metal-catalyzed reactions have substantially improved the synthetic toolbox and strongly influenced how chemists go about assembling a prospective target. First introduced in the 1970s, particularly palladium-mediated reactions offer by far the broadest substrate scope, the mildest reaction conditions, extensive functional group tolerance and thus widest applicability. However, despite their success these transformations still do not allow various desired bond formation reactions, specifically C-C couplings of highly reactive compounds bearing sensitive functional groups.The target of this research is to develop low temperature Kumada-Corriu cross coupling reactions of aryl bromides, chlorides, triflates and tosylates while widening the range of nucleophiles that can be directly coupled to include vinyl and alkyl Grignard or lithium reagents. Whereas aryl chlorides, triflates and tosylates are attractive substrate due to their low price, most Grignard and lithium reagents are easier to prepare than their respective zinc, tin or boronic acid compounds and often serve as intermediates in the preparation of the latter.

• DFG Programme: Research Fellowships
• International Connection: USA
• Host: Professor Stephen L. Buchwald, Ph.D.