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`]
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Figure 2 Electrochemical C–H selenylation (part 2)[1`]
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Figure 3 Electrochemical difunctionalization[2`]
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Figure 4 Electrochemical selenylation/cyclization (part 1)[3`]
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Figure 5 Electrochemical selenylation/cyclization (part 2)[2b]
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Figure 6 Electrochemical selenylation/cyclization (part 3)[2f]
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Figure 7 Electrochemical cross-coupling reactions[4`]
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