Iodine-Mediated Coupling of 2,2,2-Trifluorodiazoethane and Alkynes To Access Bistrifluoromethylated 1,3,5-Trienes

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.

Automated summary

We present a highly intriguing and underexplored multi-component reaction involving diazo molecules for polyene formation. This reaction involves coupling of 2,2,2-trifluorodiazoethane and aryl alkynes mediated by iodine under visible light. The reaction provides a straightforward and step-economic access to bistrifluoromethylated 1,3,5-trienes in high stereoselectivity by creating three C=C bonds in a single step under mild conditions.