COA of Formula: C21H24N2. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene, is researched, Molecular C21H24N2, CAS is 141556-42-5, about N-heterocyclic carbene adducts of alkynyl functionalized 1,3,2-dithioborolanes. Author is Boeser, Richard; Denker, Lars; Frank, Rene.
Alkynyl functionalized boron compounds are versatile intermediates in the areas of medicinal chem., materials science, and optical materials. In particular, alkynyl boronate esters [R1-CC-B(OR2)2] are of interest since they provide reactivity at both the alkyne entity, with retention of the B-C bond or alkyne transfer to electrophilic substrates with scission of the latter. The boron atom is commonly well stabilized due to (i) the extraordinary strength of two B-O bonds, and (ii) the chelate effect exerted by a bifunctional alc. We reasoned that the replacement of a B-O for a B-S bond would lead to higher reactivity and post-functionalization in the resulting alkynyl boronate thioesters [R1-CC-B(S2X)]. Access to this poorly investigated class of compounds starts form chloro dithioborolane cyclo-Cl-B(S2C2H4) as a representative example. Whereas syntheses of three coordinate alkynyl boronate thioesters [R1-CC-B(S2X)] proved to be ineffective, the reactions of NHC-adducts (NHC = N-heterocyclic carbene) of cyclo-Cl-B(S2C2H4) afforded the alkyne substituted thioboronate esters in good yield. The products NHC-B(S2C2H4)(CC-R1) are remarkably stable towards water and air, which suggests their use as boron-based building blocks for applications akin to oxygen-based boronate esters.
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Reference:
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