Diversity-Oriented Approach to CF₃CHF‑,\nCF₃CFBr‑, CF₃CF₂‑,\n(CF₃)₂CH‑, and CF₃(SCF₃)CH-Substituted Arenes from 1‑(Diazo-2,2,2-trifluoroethyl)arenes

Abstract

Arenes substituted with perfluoroalkyl\ngroups are attractive targets\nfor drug and agrochemical development. Exploiting the carbenic character\nof donor/acceptor diazo compounds, a diversity-oriented synthesis\nof perfluoroalkylated arenes, for late stage fluorofunctionalization,\nis described. The reaction of 1-(diazo-2,2,2-trifluoroethyl)­arenes\nwith HF, F/Br, F₂, CF₃H, and CF₃SH\nsources give direct access to a variety of perfluoroalkyl-substituted\narenes presenting with incremental fluorine content. The value of\nthis approach is also demonstrated for radiochemistry and positron\nemission tomography with the [¹⁸F]-labeling of CF₃CHF-, CF₃CBrF-, and CF₃CF₂-arenes\nfrom [¹⁸F]­fluoride.