Institute for Materials Chemistry and Engineering, Kyushu University , 6-1 Kasugakoen, Kasuga-shi, Fukuoka 816-8580, Japan.
CREST, Japan Science and Technology Agency (JST), 6-1 Kasugakoen, Kasuga-shi, Fukuoka 816-8580, Japan.
Org Lett. 2017 Jul 7;19(13):3450-3453. doi: 10.1021/acs.orglett.7b01423. Epub 2017 Jun 27.
Treatment of 2-phenylpyridines (or their analogs) with a 9-bicycloboranonane dimer (9-BBN dimer) in the presence of a catalytic amount of a commercially available iron salt, FeBr, gave ortho-borylated products in moderate to excellent yields with good functional group tolerance. The reaction proceeded in good yield, even in gram-scale, and also occurred at the C-H bond of heteroaromatic compounds. The cost of the C-H borylation is dramatically lower than that of a previously reported similar palladium-catalyzed reaction. The products exhibit an intramolecular B-N Lewis acid-base interaction and fluoresce in both solution and solid states due to their electron push-pull structures.
用 9-双环硼烷二聚体（9-BBN 二聚体）和商业上可用的铁盐 FeBr 处理 2-苯基吡啶（或其类似物），在催化量的铁盐存在下，得到了中等至优异产率的邻位硼化产物，具有良好的官能团耐受性。该反应即使在克级规模下也能以良好的收率进行，并且还发生在杂芳环化合物的 C-H 键上。C-H 硼化的成本明显低于以前报道的类似钯催化反应。由于其电子推拉结构，产物表现出分子内 B-N 路易斯酸碱相互作用，并在溶液和固态中都具有荧光。
