Bagutski, Viktor; Del Grosso, Alessandro; Carrillo, Josue Ayuso; Cade, Ian A.; Helm, Matthew D.; Lawson, James R.; Singleton, Paul J.; Solomon, Sophia A.; Marcelli, Tommaso; Ingleson, Michael J. published an article on January 9 ,2013. The article was titled 《Mechanistic studies into amine-mediated electrophilic arene borylation and its application in MIDA boronate synthesis》, and you may find the article in Journal of the American Chemical Society.Application of 401797-00-0 The information in the text is summarized as follows:
Direct electrophilic borylation using Y2BCl (Y2 = Cl2 or o-catecholato) with equimolar AlCl3 and a tertiary amine has been applied to a wide range of arenes and heteroarenes, yielding aryl and heterocyclic boronates in a regioselective way. In situ functionalization of the ArBCl2 products is possible with Me3SiOCOCH2NMeCH2CO2SiMe3 (TMS2MIDA), to afford bench-stable and easily isolable MIDA-boronates in moderate to good yields; pinacol and neopentylglycol esters were also prepared According to a combined exptl. and computational study, the borylation of activated arenes at 20° proceeds through an SEAr mechanism with borenium cations, [Y2B(amine)]+, the key electrophiles. For catecholato-borocations, two amine dependent reaction pathways were identified: with [CatB(NEt3)]+, an addnl. base is necessary to accomplish rapid borylation by deprotonation of the borylated arenium cation (σ complex), which otherwise would rather decompose to the starting materials than liberate the free amine to effect deprotonation. Apart from amines, the addnl. base may also be the arene itself when it is sufficiently basic (e.g., N-Me-indole). When the amine component of the borocation is less nucleophilic (e.g., 2,6-lutidine), no addnl. base is required due to more facile amine dissociation from the boron center in the borylated arenium cation intermediate. Borenium cations do not borylate poorly activated arenes (e.g., toluene) even at high temperatures; instead, the key electrophile in this case involves the product from interaction of AlCl3 with Y2BCl. When an extremely bulky amine is used, borylation again does not proceed via a borenium cation; instead, a number of mechanisms are feasible including via a boron electrophile generated by coordination of AlCl3 to Y2BCl, or by initial (heteroarene)AlCl3 adduct formation followed by deprotonation and transmetalation. In the experimental materials used by the author, we found 2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 401797-00-0Application of 401797-00-0)
2-(3,4-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 401797-00-0) belongs to hydroxy-containing compounds. Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack this functional group.Application of 401797-00-0 Organic compounds, which are often poorly soluble in water, become water-soluble when they contain two or more hydroxy groups, as illustrated by sugars and amino acid.
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