Mild and Efficient Deoxygenation of Sulfoxides to Sulfides Using HfCl₄/KBH₄System

Photocatalytic Deoxygenation of Sulfoxides Using Visible Light: Mechanistic Investigations and Synthetic Applications

“…The deoxygenation of sulfoxides to generate sulfides is a fundamental transformation in organic synthesis and biochemistry . Established methods to convert sulfoxides into sulfides involve the use of low-valent metallic species, metal hydride reagents, halide ions, and phosphorus compounds . However, these reaction systems can suffer from potential disadvantages, including the use of expensive and/or toxic reagents, difficult workup procedures, and use of harsh reaction conditions, which often limit their functional group tolerance.…”

Nickel phosphide nanoalloy catalyst for the selective deoxygenation of sulfoxides to sulfides under ambient H2 pressure

“…[21][22][23][24] A target chiral compound can be synthesized through a series of reactions including the introduction of a chiral sulfoxide and its subsequent deoxygenation. To date, many stoichiometric methods using metal hydrides, [25][26][27] hydrogen halides, [28][29][30] thiols, 31,32 and phosphines [33][34][35] have been reported for the deoxygenation of sulfoxides.…”

Hydrogenation of Sulfoxides to Sulfides under Mild Conditions Using Ruthenium Nanoparticle Catalysts

“…Among the examined TiO 2 -supported metal nanoparticles, Ru nanoparticles with a mean diameter of 1.6 nm exhibited the highest catalytic activity, affording diphenyl sulfide (2) in > 99 % yield (entry 1). The activity of Ru nanoparticles was significantly higher than that of other metal nanoparticles; Rh, Pt, and Pd nanoparticles showed very low activities (entries 2-4) while Ni, Cu, Ag, and Au nanoparticles did not show any catalytic activity at all (entries [5][6][7][8]. The catalytic activity of Ru nanoparticles was affected by the support material: TiO 2 gave the highest activity and SiO 2 was also effective but inferior to TiO 2 (entry 1 versus 9), whereas the use of hydroxyapatite (HAP) and Al 2 O 3 supports resulted in moderate to low yields of 2 (entries 10 and 11).…”

“…[3] Deoxygenation is also useful in the one-carbon homologation reaction of carbonyl compounds using active a-methylene sulfoxides as carbon sources. [4] The stoichiometric deoxygenation of sulfoxides has typically been carried out with excess amounts of sacrificial agents such as metal hydrides, [5] gaseous halogens, [6] hydrogen halides, [7] thiols, [8] and phosphines.…”