Perfluoroalkylphosphines and arsines obtained by Pd-catalyzed cross-coupling reaction with organoheteroatom stannanes

Pd-catalyzed cross-coupling reaction of organoheteroatom stannanes containing elements of the groups 15 (P, As) and 16 (Se) with perfluoroalkyl iodides (R_fI) was studied. Herein, a one-pot two-step reaction to form P–R_f, As–R_f and Se–R_f bonds is reported. The stannanes n-Bu₃SnZPh_n (Z = P, As, Se; n = 1–2) were generated in situ by the reaction of the Ph_nZ⁻ anion with n-Bu₃SnCl. The cross-coupling reactions of these stannanes with R_fI afforded C-heteroatom products, new perfluoroalkylarsines and perfluoroalkylselenides in good yields (47–90%) and perfluoroalkylphosphines in moderate yields (15–48%).