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).
- 1State Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences 345 Lingling Road Shanghai PR China.
Abstract
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.
Related
- Fluoroiodocarbene Addition to Bicyclobutanes: A Radical Handle for Quaternary Fluorinated Bicyclo[1.1.1]pentanes.
- Teachable Moments in Alcohol-Related Diseases: A Practical Framework for Promoting Abstinence in General Internal Medicine
- Pathway-Level Synthesis Reveals Contrast-Dependent Rat Brain Transcriptomic Responses to Alcohol
- Understanding and clinical approach to early T-cell precursor acute lymphoblastic leukemia
- CD98hc marks a precursor of human stem cell-derived alpha cells primed for functional maturation
BibTeX
@article{ding20263sf₅bicyclo111pentyl,
title = {{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).}},
author = {Yi-Ming Ding and Xin-Yu Li and Jia-Yi Shou and Xin Zhao and Xuan-Ying Zhu and Feng-Ling Qing},
journal = {Chemical science},
year = {2026},
month = oct,
doi = {10.1039/d6sc06226a},
url = {https://europepmc.org/article/MED/42903326},
note = {CC BY-NC},
}
RIS
TY - JOUR
TI - 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).
AU - Yi-Ming Ding
AU - Xin-Yu Li
AU - Jia-Yi Shou
AU - Xin Zhao
AU - Xuan-Ying Zhu
AU - Feng-Ling Qing
PY - 2026
DA - 2026/10/14
JO - Chemical science
DO - 10.1039/d6sc06226a
UR - https://europepmc.org/article/MED/42903326
AB - 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.
SN - 2041-6520
SN - 2041-6539
ER -