Preparation of (perfluoroalkyl)alkane thiols via Zemplén deacylation of fluorous (perfluoroalkyl)alkyl thioacetates

Article abstract of DOI:10.1016/j.jfluchem.2018.02.014

Convenient and robust synthesis of (perfluoroalkyl)alkane thiols [(C_nF_2n+1(CH₂)_mSH); m/n = 3/4,6,8,10, 4a-d; m/n = 2/6, 8; m/n = 1/1,2,3,7,8H, 12a-e] was developed starting from commercially available fluorous alcohols (1a-d, 5, 9a-e). The intermediate (perfluoroalkyl)alkyl iodides and/or sulfonates were reacted with potassium thioacetate in DMF, and the resulting thioacetates were deacetylated by a Zemplén analogue reaction. The (perfluoroalkyl)alkane thiols were obtained in good overall yields and high purity.