Hydrofunctionalisation of TASP - SF5 enamines and SF5 Vinyl sulfides

Triisopropylsilyl acetylene sulfur pentafluoride (TASP) - A precious reagent to access novel SF5 motifs

One of the hurdles in current pentafluorosulfanyl chemistry is the  use highly toxic sulfur fluorides. Recently, a variety of exciting contributions have been published to circumvent this problem using non-toxic gases like SF6 or making SF5Cl in-situ. However, these method require the handling of gases or highly toxic or corrosive reagents. We recently became interested in an alternative approach based on the exploitation of prefunctionalized triisopropylsilyl acetylene sulfur pentafluoride. We found this reagent to be a precious addition to the toolbox of pentafluorosulfanylation chemistry enabling for the preparation of unprecedented structural motifs like enamines and vinyl sulfides under benchtop conditions.

for more information see:

ChemRXiv 2022, DOI: 10.26434/chemrxiv-2022-brg1w & ChemRXiv 2022, DOI: 10.26434/chemrxiv-2022-01jhn