Organoselenium chemistry

[5][6] Selenium, in the form of organoselenium compounds, is an essential micronutrient whose absence from the diet causes cardiac muscle and skeletal dysfunction.

Organoselenium compounds are required for cellular defense against oxidative damage and for the correct functioning of the immune system.

For example, upon analysis of garlic using the technique of high-performance liquid chromatography combined with inductively coupled plasma mass spectrometry (HPLC-ICP-MS), it was found that γ-glutamyl-Se-methylselenocysteine was the major Se-containing component, along with lesser amounts of Se-methylselenocysteine.

[14] Selenocysteine, called the twenty-first amino acid, is essential for ribosome-directed protein synthesis in some organisms.

Their usefulness hinges on certain attributes, including Contrary to theoretical productions, selenium stablizes geminal carbanions slightly less than the corresponding sulfur compounds.

[17] Vinylic selenides are organoselenium compounds that play a role in organic synthesis, especially in the development of convenient stereoselective routes to functionalized alkenes.

[18] Although various methods are mentioned for the preparation of vinylic selenides, a more useful procedure has centered on the nucleophilic or electrophilic organoselenium addition to terminal or internal alkynes.

[19][20][21][22] For example, the nucleophilic addition of selenophenol to alkynes affords, preferentially, the Z-vinylic selenides after longer reaction times at room temperature.

Conversely, vinylic selenides can be prepared by palladium-catalyzed hydroselenation of alkynes to afford the Markovnikov adduct in good yields.

There are some limitations associated with the methodologies to prepare vinylic selenides illustrated above; the procedures described employ diorganoyl diselenides or selenophenol as starting materials, which are volatile and unstable and have an unpleasant odor.