Iodine-Mediated Coupling of 2,2,2-Trifluorodiazoethane and Alkynes To Access Bistrifluoromethylated 1,3,5-Trienes
Yangjinxiu Zhou, Tengfei Pang, Yu Liu, Fangrui Zhong, Guojiao Wu
Abstract
Multi-component reaction of higher degree ultilization of diazo molecules for polyene formation is highly intriuging but still underexplored. We present herein an unprecedented coupling of 2,2,2-trifluorodiazoethane and aryl alkynes mediated by iodine under visible light. The multi-component reaction involving two diazo units and two alkyne units provides a straightforward and step-economic access to bistrifluoromethylated 1,3,5-trienes in high stereoselectivity by creation of three C═C bonds in a single step under mild conditions.
Topics & Concepts
DiazoChemistryPolyeneStereoselectivityIodineAlkyneComponent (thermodynamics)ArylCoupling reactionMoleculeCoupling (piping)Combinatorial chemistryPhotochemistryMedicinal chemistryOrganic chemistryCatalysisAlkylPhysicsEngineeringThermodynamicsMechanical engineeringFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods