Tajuddin, Hazmi published the artcileIridium-catalyzed C-H borylation of quinolines and unsymmetrical 1,2-disubstituted benzenes: insights into steric and electronic effects on selectivity, Application of Methyl 2,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, the publication is Chemical Science (2012), 3(12), 3505-3515, database is CAplus.
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.
Chemical Science published new progress about 1417036-37-3. 1417036-37-3 belongs to esters-buliding-blocks, auxiliary class Boronic acid and ester, name is Methyl 2,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, and the molecular formula is C12H10F2Si, Application of Methyl 2,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate.
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