Spotlights on Recent JACS Publications.

作者：C. Brownlee · 发表于：Journal of the American Chemical Society · 年份：2021 · DOI：10.1021/jacs.1c08918 · 研究领域：Medicine

Water’s promise as a sustainable solvent for organic and organometallic chemistry is tempered by its significant drawbacks: nonpolar organic substrates are poorly soluble in water, and water can decompose organometallic compounds through protodemetalation. Micelle-forming surfactants could help overcome these issues. However, this approach has not been widely adopted, partly because micelles’ role in reaction mechanisms is not well understood. Suzanne Blum and Hannah Peacock use the power of fluorescence microscopy to investigate this question (DOI: 10.1021/jacs.2c00421). Incorporating boron dipyrromethene fluorphores as representative organic molecular “cargo”, the researchers imaged micelles attaching to micron-scale zinc particles. They observed that micelles do not adhere immediately to the zinc particles but built up over time, remaining in local regions of the particles for the duration of imaging experiments. Two-color fluorescence crossover experiments further showed that micelles on the zinc particles exchanged molecular contents with micelles in solution. Aging of the micellar solutions and rate of exchange while on the surface of the zinc particles suggest that micelle mass transport processes may contribute to overall reaction barriers in sustainable organozinc cross-coupling reactions in water, the authors say. These findings suggest new approaches that could improve bench-scale synthetic reactions involving micellar preparations of organozinc compounds. Christen...