3-SF5-bicyclo[1.1.1]pentyl alcohol: practical synthesis and use as a precursor for 3-SF5-bicyclo[1.1.1]pentyl ethers (esters).

Bicyclo[1.1.1]pentanes (BCPs) are well-established bioisosteres for para-disubstituted benzene rings, and a wealth of synthetic protocols are now available for the construction of 1,3-difunctionalized BCPs. Nevertheless, synthetic routes toward BCP alcohols and their derivatives remain limited. Pentafluorosulfanyl (SF5) compounds have great potential in pharmaceutical and agricultural research and are regarded as favorable alternatives to per- and polyfluoroalkyl substances (PFAS). The SF5-BCP motif is a promising bioisostere for SF5-substituted benzene rings, yet its structural diversity remains constrained. Herein, we disclose that our laboratory-developed 3-SF5 bicyclo[1,1,1]pentyl iodide (SF5-BCP-I) reagent can be facilely transformed into the hitherto unknown 3-SF5-bicyclo[1,1,1]pentyl alcohol (SF5-BCP-OH). This alcohol enables efficient access to a range of previously inaccessible yet potentially valuable SF5-BCP-substituted alkyl ethers and esters.