The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Preparation of thermally stable and soluble mesitylcopper(I) and its application in organic synthesis》. Authors are Tsuda, Tetsuo; Yazawa, Tetsuo; Watanabe, Katsuhiko; Fujii, Tomoyuki; Saegusa, Takeo.The article about the compound:Mesitylcopper(I)cas:75732-01-3,SMILESS:[Cu]C1=C(C)C=C(C)C=C1C).Application of 75732-01-3. Through the article, more information about this compound (cas:75732-01-3) is conveyed.
Mesitylcopper(I) (I) was prepared and isolated by the reaction of mesitylmagnesium bromide and CuCl. I is a unique organocopper(I) compound, which is thermally stable up to 100° and is highly soluble in common organic solvents. I may be utilized in organic synthesis as an efficient metalation reagent and as a useful “”holding group”” in mixed lithium cuprate reagents. I metalated amine, alc. and mercaptan to produce Cu(I) amide, alkoxide and mercaptide, resp. I reacted with alkyllithium (RLi) to form a soluble mixed cuprate reagent II, which effected a selective conjugate addition of the R group to cyclohexenone and trans-2-hexenal. A reagent produced by the reaction of I and LiAlH4 effected the regioselective 1,4-reduction of cyclohexenone in a mixed solvent of THF and (Me2N)3PO.
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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com