|McNally, Prier & MacMillan are also on the trail of high-throughput organic reaction discovery in what this blog likes to call lazy chemistry (DOI). The main theme is serendipity and the quotes are fantastic: "Recently, we questioned whether serendipity could be forced or simulated to occur on a predictable basis in the realm of reaction discovery, thereby providing a reliable platform to access valuable transformations or unexpected pathways" and "assuming that serendipity is governed by probability...".|
The research protocol looks very similar to the one described by Hartwig (DOI) just 4 months ago and features a 96-well plate that was filled horizontally and vertically with up to 19 different simple organic substrates such as benzaldehyde or pyridine. A known reaction type between any two reaction partners should not be obvious. A solvent containing transition-metal catalysts / ligands was then added and after exposure to a 26 watt fluorescent lamp and a certain reaction time the reaction product was analysed by GC-MS and a MS library. The article boasts up to a thousand reactions per day can be screened in this semi automatic way.
The main find was a novel carbon-carbon coupling reaction between 1,4-dicyanobenzene and N-phenyl-pyrrolidine using photoredox catalyst iridium tris(2-phenylpyridine).