Pentafluorosulfanylation of Aliphatic Substrates

Amine–borane complex-initiated SF5Cl radical addition on alkenes and alkynes

“…Moreover, this method leads to significantly higher yields in shorter reaction times compared to the previous methods. Since this first report, this reaction has been extensively used to obtain a wide range of SF 5 -containing aliphatic derivatives, and represents the most versatile route towards pentafluorosulfanylated aliphatic compounds [28]. However, some limitations have emerged from the Dolbier protocol.…”

“…Although the number of synthetic routes towards the SF 5 substituent remains limited, a few methods have been developed in the past 20 years in order to include a SF 5 moiety on various organic substrates [ 27 – 28 ]. The main strategy towards pentafluorosulfanylated aliphatic compounds, reported for the first time by Dolbier and co-workers in 2002, is the Et 3 B-mediated radical addition of SF 5 Cl on alkenes and alkynes ( Scheme 1 ) [ 29 – 30 ].…”

A SF5 Derivative of Triphenylphosphine as an Electron-Poor Ligand Precursor for Rh and Ir Complexes

“…In addition, phenyl groups with SF 5 moieties at both meta and para positions exhibit a stronger electron-withdrawing effect according to Hammett constants (σ m = 0.61, σ p = 0.68), when compared with a fluorine substituent ( F = 0.45, R = −0.39, σ m = 0.34, σ p = 0.06) or the trifluoromethyl group ( F = 0.38, R = 0.16, σ m = 0.43, σ p = 0.54) [ 21 ]. Despite the increasing interest on SF 5 -containing compounds described in literature and their applications as building blocks in many fields such as agrochemical, medicinal, or materials chemistry [ 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 ], SF 5 derivatized ligands in transition metal complexes are still rare [ 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 ]. Examples mainly focus on C^N cyclometalated ligands which contain the SF 5 moiety in their phenyl rings in order to stabilize iridium(III) [ 34 , 35 , 36 , 37 ] or platinum(II) [ 38 ] complexes with optoelectronic properties.…”

Radical 1,5-Chloropentafluorosulfanylation of Unactivated Vinylcyclopropanes and Transformation into α-SF5 Ketones

“…. Nevertheless, the number of SF 5 -containing molecules is still rather small, and a particular focus is given to SF 5 -substituted (hetero)­aromatics, while aliphatic SF 5 derivatives are less investigated . In this context, expanding the chemical space of SF 5 -containing aliphatic compounds offers wide opportunities.…”