A decade updates (2011–2020): Reduction of sulfoxides to sulfides

Reduction of sulfoxides catalyzed by the commercially available manganese complex MnBr(CO)5

“…The reduction of sulfoxides to the corresponding sulfides is one of the most important chemical transformations in organic chemistry, due to the relevance of sulfides as intermediates in the synthesis of many biological, pharmaceutical and natural active molecules. Over the years, several methods have been developed to synthesize sulfides by reducing sulfoxides using a variety of catalysts containing different metals, including Mo, [1][2][3][4][5][6][7] Re, [8][9][10][11][12] Fe, 13,14 Zn, [15][16][17] Cu, 18 Ti, 19 Nb, 20,21 Co, 22 B, 23,24 etc., [25][26][27] by employing silanes, boranes, phosphites and H 2 as reducing agents.…”

Visible light induced deoxygenation of sulfoxides with isopropanol

“…Established processes for the deoxygenation of sulfoxides to sulfides typically require molar excess of reducing agents such as halide ions, 5 sulfur compounds, boron compounds, phosphorus compounds, 6 silicon compounds, 7 low-valent metals, metal hydride reagents, and so on. 8 Catalytic hydrogenation and electrochemical strategies have also been employed for the deoxygenation of sulfoxides (Scheme 1a). 9 As eco-friendly and low-cost reducing agents, 10 alcohols have drawn considerable attention in the reduction of sulfoxides to sulfides (Scheme 1b).…”

Metal-free photo-induced sulfidation of aryl iodide and other chalcogenation

“…For instance, transition metal-catalyzed decarbonylation of thioester from readily available carboxylic acids has been regarded as another noteworthy strategy for achieving C–S bond formation ( Figure 2B ). ( Ichiishi et al, 2018 ; Bie et al, 2021 ; Han Cao et al, 2021 ; Liu and Szostak, 2021 ) Reduction of sulfoxides also serves as a direct route to sulfides ( Shiri and Kazemi, 2017 ; Lin et al, 2021 ; Zhang 2022 ). The synthesis of aryl sulfides using phenylboronic acid as substrate requires the participation of magnetic nanoparticles or expensive transition metals ( Xu et al, 2012 ; Rostami et al, 2015a ; Rostami et al, 2015b ; Amiri et al, 2016a ; Amiri et al, 2016b ; Rostami et al, 2017 ; Wang et al, 2017 ; Cheng et al, 2018 ; Farzin et al, 2018 ; Atashkar et al, 2019 ; Gavhane et al, 2019 ; Khakyzadeh et al, 2019 ).…”