High-Throughput Synthesis of (<i>S</i>)-α-Phellandrene through Three-Step Sequential Continuous-Flow Reactions
Samuel Miller, Haruro Ishitani, Yuichi Furiya, Shu̅ Kobayashi
Abstract
The combination of continuous-flow processing with heterogeneous catalysts allows for efficient, sustainable, multistep synthesis. Here, we report the continuous-flow synthesis of a valuable terpene product, phellandrene, from a readily available natural feedstock. The protocol consists of selective hydrogenation using a highly active and stable supported platinum catalyst, dehydrative hydrazone formation, followed by the Shapiro reaction. Appropriate design of the reactor allowed for high productivity and space–time yield. Phellandrene was synthesized on a 30-g scale over 6 h, giving high yields, purity, and productivity.
Topics & Concepts
Flow chemistryYield (engineering)Continuous flowCatalysisRaw materialChemistryContinuous reactorThroughputReaction conditionsOrganic chemistryCombinatorial chemistryComputer scienceMaterials scienceBiochemical engineeringEngineeringTelecommunicationsWirelessMetallurgyInnovative Microfluidic and Catalytic Techniques InnovationChemical synthesis and alkaloids