Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates

Abstract

The construction of a C-S bond is a powerful strategy for the synthesis of sulfur containing compounds including sulfides, sulfoxides, and sulfones. Recent methodological developments have revealed lots of novel protocols for C-S bond formation, providing easy access to sulfur containing compounds. Unlike traditional Ullmann typed C-S coupling reaction, the recently developed reactions frequently use non-halide compounds, such as diazo compounds and simple arenes/alkanes instead of aryl halides as substrates. On the other hand, novel C-S coupling reaction pathways involving thiyl radicals have emerged as an important strategy to construct C-S bonds. In this review, we focus on the recent advances on the synthesis of sulfides, sulfoxides, and sulfones from non-halide substrates involving C-S bond construction.

A review on the latest progress of C‐S cross‐coupling in diaryl sulfide synthesis: Update from 2012 to 2021

“…As a helpful tool, the synthesis of diaryl sulfide derivatives is significant and has been the subject of several kinds of research. [10][11][12][13][14][15] Figure 1 represents the biologically active aryl sulfide compounds.…”

Metal-free multicomponent synthesis of novel macrocyclic tetrathiadienes with cyano and amino groups

“…[1][2][3] Unlike the traditional Ullmann and Chan Lam coupling reactions, a simple strategy of a non-halide pathway to sulfur compounds is the use of diaryl suldes as starting substrates. [4][5][6] Another approach is based on the formation of a C-S bond by transition metal-catalyzed thiomethylation via condensation of thioacetals with CH-acids. [7][8][9] Meanwhile, the growing demand for new materials, increasing complexity of molecular drug targets, and chemotherapeutic drug and antibiotic resistance account for the increasing relevance of new thiamacrocyclic compounds.…”

“… 1–3 Unlike the traditional Ullmann and Chan Lam coupling reactions, a simple strategy of a non-halide pathway to sulfur compounds is the use of diaryl sulfides as starting substrates. 4–6 Another approach is based on the formation of a C–S bond by transition metal-catalyzed thiomethylation via condensation of thioacetals with CH-acids. 7–9 …”

Diaryl Sulfide Derivatives as Potential Iron Corrosion Inhibitors: A Computational Study

“…Sulfur-containing compounds, such as sulfides, sulfoxides, and sulfones, constitute a large portion of pharmaceutical drugs that possess various biological activities [ 17 ]. For example, Chan et al assessed the antiviral activity against HIV-1 of a series of 2-amino-6-arylthiobenzonitriles and their sulfoxides and sulfones derivatives [ 18 ].…”