Trivinylboroxin

Trivinylboroxin is the organoboron compound, consists of a six-membered ring with boron and oxygen atoms, with vinyl groups attached to each boron atom. It is the synthetic equivalent of vinyl boronic acid in the Suzuki reaction.

Trivinylboroxin can be prepared from trimethyl borate and vinylmagnesium bromide, but its isolation is difficult due to its rapid polymerization

Applications
Trivinylboroxine is usually used in organic chemistry to produce styrene derivatives by the Suzuki reaction. However, trivinylboroxine rapidly decomposes with polymerization during storage, which makes its use in laboratory practice difficult.


 * New Organolithium Addition Methodology to Diversely Functionalized Indoles.svg

Reactions in the presence of copper(II) acetate with trivinylboroxine lead to the formation of vinyl esters.


 * Synthesis of vanillin vinyl ether.svg

In organic synthesis, a complex of trivinylboroxine with pyridine is often used (O'shea reagent). This complex is a solid that can be stored undisturbed at low temperatures (-20 ℃) without evidence of decomposition. The O'shea reagent is also used for the synthesis of vinyl-substituted heterocyclic compounds.


 * Synthesis of naphthyridine.svg

The preparation of ortho-substituted styrenes using trivinylboroxine pyridine complex is of practical importance, for example, in this way benzo-fused rings can be obtained. Also, ortho-substituted styrene derivatives are important substances for the production of polymer materials. Traditional methods for generating styrenes typically involve dehydration under acidic conditions or elimination under basic conditions to form the double bond.