Dawid Lichosyt and Aleksandra Zasada have introduced a novel approach in organic synthesis that significantly improves hydrocyanation while controlling regioselectivity. This novel approach is entirely transition metal free. It’s super duper economical, expected to be around 2,500 times cheaper than conventional transition metal-based methods. The researchers’ results would be an important step towards establishing methodologies for hydrofunctionalization. These strategies have long been key for the synthesis of nitriles for well over seventy years.
This new methodology provides a simple, efficient route to synthesize vinyl nitriles. It goals for a superior precision, achieving an amazing 97% yield over 40 illustrations. Furthermore, the approach demonstrates a rare anti-stereoselectivity of up to 20:1, showcasing its precision and effectiveness. The user-friendly system greatly improves regioselectivity. It exhibits wide functional group tolerance, rendering it a highly useful and versatile tool for organic chemists.
Regioselectivity control is a challenge in hydrofunctionalization and one of the greatest hurdles encountered in hydrocyanation. Lichosyt and Zasada have approached this by using tetrabutylammonium cyanide (TBACN) as a replacement of phosphine (PPh3). This powerful new replacement enables orthogonally regioselective formation of distinct yet complementary (al)kylated regioisomers. By deep optimization, the two catalysts—phosphine and amine—function in a completely orthogonal fashion enabling selective switches in regioselectivity.
This method leverages a simple two-step, one-pot dual system that significantly reduces the steps needed to prepare useful vinyl nitriles. Moreover, it opens the door to new and exciting research opportunities in organic synthesis. The transition-metal-free nature of this method addresses one of the key challenges facing the development of greener methods for chemical production.