Organometallic species organomercury

A general method for the synthesis of organomercurials is the transmetallation of mercury (II) salts with other organometallic species. Organolithium and -magnesium compounds continue to be widely employed for the preparation of complexes with formula RHgX or HgR2 (see equation 1). 

Early versions of the Heck reaction employed organomercury compounds rather than organic halides. This process results in net reduction of palladium, so a stoichiometric amount was used. Other organometallic species may be used in place of organomercury compounds, such as boronic acids 5.199. In the presence of an oxidant, a catalytic process is possible, delivering Heck-like products (Scheme 5.55). ... 

The relatively low reactivity of the RHgX reagent is shown by acylation with RCOCl this gives a ketone that is stable to further attack by the organometallic species. The organomercury reagents with their very weak Hg—C bonds are a useful source of radicals. Once Ae first R is released, the remaining R is very weakly hound (Eq. 14.31), and so both radicals are effectively released at the same time. 

The separation of organomercury was conducted by using a SB-methyl-100 capillary column and pure CO2 as the mobile phase. FID and atomic fluorescence were used for detection. The same column was also used for separation of mercury, arsenic, and antimony species using carbon dioxide as the mobile phase. A chelating reagent, bis(trifluoroethyl)dithiocarbamate, was used in this case to convert the metal ions to organometallic compounds before the separation. The detection limit of FID was 7 and 11 pg for arsenic and antimony, respectively. 

---