In a typical chemical reaction in the pharmaceutical industry, solvent use accounts for 60-90% of waste created. Additionally, organic solvents play a dominant role in the overall toxicity profile of most processes and are therefore the chemicals of greatest concern. Strategies to minimize the economic and environmental footprint of organic solvents are of utmost interest. One alternative to organic solvents follows the lead of Nature: water. To circumvent the solubility issues, surfactants by the group of Prof. Lipshutz offer an opportunity to enable organic reactions to proceed efficiently in water at room temperature. These environmentally benign surfactants spontaneously self-aggregate in water and the resulting micellar arrays serve as nanoreactors. We will disclose applications of micellar catalysis for the most important reaction types performed in the pharmaceutical industry (e.g. transition-metal-catalyzed reactions such as Buchwald-Hartwig aminations, Suzuki and Negishi couplings). Often times such reactions in water display advantages compared to conventional reaction conditions in organic solvents. In addition, we will disclose for the first time a new additive, which enables chemical reactions to proceed in water with unprecedented short reaction times. For examples Buchwald-Hartwig couplings, which are published to proceed in organic solvents at elevated temperatures (e.g. &gt; 100°C) and reaction times in the range of hours, proceed within minutes at room temperature in water using this new additive. Also non metal-catalyzed reactions like peptide couplings will be disclosed. Again, unprecedented short reaction times in the range of minutes were observed.

Organic chemistry in water: Applications in the pharmaceutical industry

253rd National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.