Palladium-catalysed C-N bond formation: New tools for synthesis

ORGN 127

Jay Chauhan, j.chauhan@bath.ac.uk1, Michael C. Willis, m.c.willis@bath.ac.uk1, and William G. Whittingham2. (1) Department of Chemistry, University of Bath, Building 1 South, Claverton Down, Bath, BA2 7AY, United Kingdom, (2) Department of Chemistry, Syngenta, Jealott's Hill, Bracknell, Berkshire, RG42 6EY, United Kingdom
Enamines are classically formed by the condensation of carbonyl motifs and secondary amines. These highly reactive enamines can be employed in numerous transformations such as carbon-carbon bond constructions and synthesis of heterocycles. Our approach to enamines circumvents the typical condensation reaction by employing palladium catalysis to couple amines to vinyl halides, shown below. This in situ enamine generation (1) is trapped by electrophiles such as aldehydes, diazo substrates and activated olefins. This would allow complex molecules to be built from simple substrates in a single reaction. The poster will describe our results from the investigation of this one pot methodology where vinyl halides are coupled to a variety of electrophiles.

 

Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 14 March 2005 Convention Center -- Sails Pavilion, Sci-Mix

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005