Key words
electrochemistry - organoselenium compounds - selenylation - difunctionalization - cyclization - cross-coupling
Organoselenium chemistry has remained a field of persistent exploration ever since selenium was recognized as an essential trace element within the human body. The significance of organoselenium compounds has experienced a substantial surge, particularly since the 1970s, marked by the discovery of numerous intriguing compounds boasting diverse applications in synthesis and biology. Notably, among these compounds, diselenides have emerged as immensely valuable organic entities. The presence of Se–Se bonds confers their distinctive chemical attributes, enabling their involvement in a range of reactions as electrophilic (RSe+), nucleophilic (RSe–), or free-radical (RSe•) agents.
Over the past decades, advancements have propelled the synthesis of organoselenium molecules, a field often characterized by the routine utilization of costly catalysts and a variety of transition metals. This has spurred an ongoing quest to unearth more economical and environmentally friendly methodologies for generating selenium-containing compounds. Notably, recent breakthroughs in this pursuit have culminated in the development of an efficient and ecologically sound electrochemical selenylation process.
Electrochemistry has become an important strategy in organic synthesis, leading to the development of a multitude of beneficial transformations. One of its strengths lies in its capacity to induce carbon–carbon and carbon–heteroatom bond formation through anodic oxidation, all within an environment free from external oxidants. Notably, the domain of electrochemical synthesis has witnessed a surge in its utilization within the context of the formation of organoselenium compounds. Within the scope of this graphical review, our aim is to provide readers with an extended collection of instances exemplifying the utilization of electrochemical techniques in the synthesis of organoselenium compounds.
Figure 1 Electrochemical C–H selenylation (part 1)[1`]
[b]
[c]
[d]
[e]
[f]
[g]
[h]
[i]
[j]
[k]
[l]
Figure 2 Electrochemical C–H selenylation (part 2)[1`]
[n]
[o]
[p]
Figure 3 Electrochemical difunctionalization[2`]
[b]
[c]
[d]
[e]
[f]
[g]
[h]
[i]
[j]
Figure 4 Electrochemical selenylation/cyclization (part 1)[3`]
[b]
[c]
[d]
[e]
[f]
[g]
[h]
[i]
Figure 5 Electrochemical selenylation/cyclization (part 2)[2b]
,
[3`]
[k]
[l]
[m]
[n]
[o]
[p]
[q]
[r]
[s]
Figure 6 Electrochemical selenylation/cyclization (part 3)[2f]
,
[3`]
[u]
[v]
[w]
[x]
[y]
[z]
Figure 7 Electrochemical cross-coupling reactions[4`]
[b]
[c]
[d]
[e]
