Development of intramolecular metal-mediated cascade reactions: Hydrostannation/Stille coupling cascade reactions performed in ionic liquids

ORGN 455

William R. Shay, Julius N. Ngwendson, and Relindis Y. Mawo. Department of Chemistry, University of North Dakota, Grand Forks, ND 58202

A recent development in organic synthesis is the use of more environmentally friendly reaction conditions. Our research in this area is focused on the reduction of organic solvents in use and reduction of hazardous waste generated by replacing single-step reactions with multi-reaction cascade processes and replacing traditional organic solvents with room-temperature ionic liquids. The development of a metal-mediated intramolecular cascade hydrostannation/ Stille coupling reaction and the application of this methodology toward the synthesis of exocyclic-1,3-dienes will be presented. The cascade reaction has been investigated in both organic solvents and ionic liquids. In some examples, the ionic liquid acts both as the solvent and as a basic additive. Substoichiometric quantities of tin-based reagents have been utilized in the cascade process, thereby, making the process more environmentally attractive. Possible mechanistic pathways, including the effect of the ionic liquid, will be presented.

Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions 8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster Division of Organic Chemistry The 226th ACS National Meeting, New York, NY, September 7-11, 2003