The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1,3-Dimesityl-1H-imidazol-3-ium tetrafluoroborate( cas:286014-53-7 ) is researched.Electric Literature of C21H25BF4N2.Hans, Morgan; Lorkowski, Jan; Demonceau, Albert; Delaude, Lionel published the article 《Efficient synthetic protocols for the preparation of common N-heterocyclic carbene precursors》 about this compound( cas:286014-53-7 ) in Beilstein Journal of Organic Chemistry. Keywords: imidazolium preparation; imidazolinium preparation microwave irradiation; cyclization; experimental procedure; imidazolinium salt; imidazolium salt; microwave heating. Let’s learn more about this compound (cas:286014-53-7).
The one-pot condensation of glyoxal, two equivalent of cyclohexylamine, and paraformaldehyde in the presence of aqueous HBF4 provided a straightforward access to 1,3-dicyclohexylimidazolium tetrafluoroborate (ICy·HBF4). The 1,3-dibenzylimidazolium tetrafluoroborate (IBn·HBF4) was obtained along the same lines. To synthesize 1,3-diarylmidazolium salts, e.g., I it was necessary to isolate the intermediate N,N’-diarylethylenediimines such as N,N’-dimesitylethanediimine, N,N’-bis(2,6-diisopropylphenyl)ethanediimine and N,N’-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)ethanediimine prior to their cyclization. Although this addnl. step required more time and reagents, it led to a much more efficient overall process. It also proved very convenient to carry out the synthesis of imidazolinium salts, e.g., II in parallel to their imidazolium counterparts via the reduction of the diimines into diammonium salts. The critical assembly of the C2 precarbenic unit was best achieved with paraformaldehyde and chlorotrimethylsilane in the case of imidazolium derivatives, e.g., I, whereas the use of tri-Et orthoformate under microwave irradiation was most appropriate for the fast and efficient synthesis of imidazolinium salts e.g., II. This strategy was applied to the synthesis of six common N-heterocyclic carbene precursors, namely, 1,3-dimesitylimidazolium chloride (IMes·HCl), 1,3-dimesitylimidazolium tetrafluoroborate (IMes·HBF4), 1,3-dimesitylimidazolinium chloride (SIMes·HCl), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IDip·HCl or IPr·HCl), 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride (SIDip·HCl or SIPr·HCl), and 1,3-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)imidazolium chloride (IDip·HCl or IPr*·HCl).
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Reference:
Bromide – Wikipedia,
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