Development of intramolecular metal-mediated cascade reactions: Hydroboration/Suzuki coupling cascade reactions performed in ionic liquids

ORGN 454

William R. Shay, Relindis Y. Mawo, and Julius N. Ngwendson. 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 hydroboration/ Suzuki coupling reaction and our efforts toward the synthesis of macrocycles containing conjugated E,E- or E,Z-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. Possible mechanistic pathways, including the effect of the ionic liquid, will be presented.