Radical Addition of 2,2,2-Trifluoroethyl Iodide to Terminal Alkenes

Polyfluorinated Ethanes as Versatile Fluorinated C2-Building Blocks for Organic Synthesis

“…162 AIBN or benzyl peroxide-catalyzed addition of CF 3 CH 2 I to terminal alkenes followed by sodium borohydride reduction represents a very useful two-step protocol for the preparation of various alkanes 50j having trifluoromethyl group at the end of the chain (Scheme 60). 163 AIBN-catalyzed radical addition of 1,1-difluoro-1-iodoethane to hexene-1 confirmed additionally the efficiency of this protocol. The corresponding adduct 25r was prepared in high yield.…”

“…AIBN or benzyl peroxide-catalyzed addition of CF 3 CH 2 I to terminal alkenes followed by sodium borohydride reduction represents a very useful two-step protocol for the preparation of various alkanes 50j having trifluoromethyl group at the end of the chain (Scheme ) …”

Scientific surgery

“…We then heated 1,1,1‐trifluoro‐4‐iodooctane (compound 15 in the Supporting Information) at 80 °C for 8.0 h in the presence of Zn metal18 and acetic acid to remove the iodide atom in the molecule to give 7 in 73 % yield. The 13 C NMR spectrum revealed signals at δ =127.33 (q, J =274.0 Hz) and 33.75 ppm (q, J =28.0 Hz), consistent with the replacement of one of the methyl groups with a CF 3 group 19. The observation of a signal at m / z 168 in the EI‐MS spectrum further confirmed the successful synthesis of compound 7 .…”

Synthesis of 11β-Perfluorohexylestradiol

“…Thus it was shown that the radical 16a formed from 2,2,2-trifluoroethyliodide adds with difficulty to electron-rich olefins . We have observed that tertiary trifluoromethylated radical 16b , derived from xanthates, reacted sluggishly with allyltributyltin under atypical radical reaction conditions .…”