Year: 2025
Type: article
Abstract: The highly strained 1,3-disubstituted bicyclo [1.1.1] pentane (BCP) was identified as a bioisostere of para-disubstituted aromatics due to its ability to enhance the solubility and metabolic stability of parent compounds. In addition, pentafluorosulfanyl (SF5)-containing compounds have received great attention in medicinal chemistry, particularly for pentafluorosulfanylarenes (SF5-Ar). Consequently, pentafluorosulfanyl bicyclo [1.1.1] pentane (F5S-BCP) could be considered as the bioisostere of pentafluorosulfanyl phenyl and might have potential applications in drug discovery. Our group has reported the first F5S-BCP radical precursor, pentafluorosulfanyliodobicyclo [1.1.1] pentane (F5S-BCP-I), and its radical addition with alkenes and alkynes. Herein, we describe the synthesis of pentafluorosulfanyl bicyclo [1.1.1] pentyl (hetero)aryl ketones through an aryl diazonium salt initiated radical reaction of N-tert-butyl-α-phenylnitrone (PBN) with F5S-BCP-I.
Source: Scientia Sinica Chimica
Authors: Xin Zhao, Jia-Yi Shou, Feng-Ling Qing
Language: English
Subfield: Pharmaceutical Science
Domain: Life Sciences
Open Access status: bronze
OpenAlex ID: W4409082400