Tajuddin, Hazmi; Harrisson, Peter; Bitterlich, Bianca; Collings, Jonathan C.; Sim, Neil; Batsanov, Andrei S.; Cheung, Man Sing; Kawamorita, Soichiro; Maxwell, Aoife C.; Shukla, Lena; Morris, James; Lin, Zhenyang; Marder, Todd B.; Steel, Patrick G. published an article in 2012, the title of the article was Iridium-catalyzed C-H borylation of quinolines and unsymmetrical 1,2-disubstituted benzenes: insights into steric and electronic effects on selectivity.Reference of 2-(3-Methoxy-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane And the article contains the following content:
Borylation of quinolines provides an attractive method for the late-stage functionalization of this important heterocycle. The regiochem. of this reaction is dominated by sterptsic factors but, by undertaking reactions at room temperature, an underlying electronic selectivity becomes apparent, as exemplified by the comparative reactions of 7-halo-2-methylquinoline and 2,7-dimethylquinoline which afford variable amounts of the 5- and 4-borylated products. Similar electronic selectivities are observed for nonsym. 1,2-disubstituted benzenes. The site of borylation can be simply estimated by anal. of the 1H NMR spectrum of the starting material with preferential borylation occurring at the site of the most deshielded sterically accessible H or C atom. Such effects can be linked with C-H acidity. While DFT calculations of the pKa for the C-H bond show good correlation with the observed selectivity, small differences suggest that related alternative, but much more computationally demanding values, such as the M-C bond strength, may be better quant. predictors of selectivity. The experimental process involved the reaction of 2-(3-Methoxy-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 1417036-28-2).Reference of 2-(3-Methoxy-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
The Article related to quinoline derivative borylation iridium catalyst regiochem steric electronic effect, mol structure borylated quinoline preparation, Organometallic and Organometalloidal Compounds: Boron Compounds and other aspects.Reference of 2-(3-Methoxy-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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