Sodium dithionite initiated reaction of pent-4-en-1-amines with fluoroalkyl iodides for the synthesis of 2-fluoroalkyl pyrrolidine derivatives

Pent-4-en-1-amines are reactive to fluoroalkyl iodides with respect to sodium dithionite initiated free radical addition reactions. We report here the development of a novel and efficient synthesis of 2-fluoroalkyl pyrrolidine derivatives by sodium dithionite initiated one-pot reaction of pent-4-en-1-amines bearing various protecting groups with fluoroalkyl iodides. Among which, the N-benzyl-pent-4-en-1-amine exhibited the best tolerance toward the reaction condition in the present study, affording the desired adducts 3 in moderate to good yields of 65–85%.

Graphical abstractAn efficient synthesis of 2-fluoroalkyl pyrrolidines was developed by the sodium dithionite initiated one-pot reaction of N-benzyl-pent-4-en-1-amines with fluoroalkyl iodides in moderate to good yields.Figure optionsDownload full-size imageDownload as PowerPoint slide