B(C₆F₅)₃‐Catalyzed Deoxygenation of Sulfoxides and Amine N‐Oxides with Hydrosilanes

Abstract

An efficient strategy for the deoxygenation of sulfoxides and amine N‐oxides by using B(C6F5)3 and hydrosilanes was developed. This method provided the corresponding aromatic and aliphatic products in good to high yields and showed good functional‐group tolerance under mild conditions.

I2/K2S2O8: An Unprecedented Deoxygenating System for N‐Oxides and Sulfoxides

“…Other reagents such as sulfur reagents, phosphorus reagents, were also used for deoxygenation. On other side, different catalytic systems have been employed for the deoxygenation of sulfoxide viz., B(C 6 F 5 ) 3 /hydrosilanes, I 2 , Zn(OTf) 2 /boranes, ruthenium nanoparticles, silane/MoO 2 Cl 2 , oxo complexes, gold nanoparticles, SOCl 2 , and Fe powder, etc.…”

“…[1] Very recently, scientists found the new role of Noxides as a oxidant in gold catalyzed reactions of alkynes. [2] During the last few decades, many types of methods have been developed to reduce N-oxides to their corresponding amines, among them, a variety of catalysts including boronic acid, [3] B(C 6 F 5 ) 3 /hydrosilanes, [4] CuI, [5] Zn/NH 4 Cl, [6] PdÀ C/ HCOONH 4 , [7] In/NH 4 Cl, [8] etc have been used. Other reagents such as sulfur reagents, [9] phosphorus reagents, [10] were also used for deoxygenation.…”

Nano CoCuFe2O4‐catalyzed coupling reaction of arylboronic acid with amines and thiols: An atom‐economic and ligand‐free route to access unsymmetrical amines and sulfides

“…The residue was purified by column chromatography on silica gel ( n ‐hexane/EtOAc, 75:25). All products were known compounds and were identified by comparison of their 1 H NMR spectra with those of authentic samples …”

B(C6F5)3‐Catalyzed Reduction of Cyclic N‐Sulfonyl Ketimines

“…As an alternative to H 2 in the reduction, hydrosilanes always turn out to be more convenient and variable. In fact, the FLPs can also activate the Si–H bond apart from activating the H 2 , . In 2000, Piers reported an effective hydrosilation of benzaldimines and ketimines which was catalyzed by B(C 6 F 5 ) 3 in presence of PhMe 2 SiH for the first time .…”