Zhang Hua, Hagihara Shinya, Itami Kenichiro
Institute of Transformative Bio-Molecules (WPI-ITbM) and, Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602 (Japan).
JST-ERATO, Itami Molecular Nanocarbon Project, Nagoya University, Chikusa, Nagoya 464-8602 (Japan).
Chemistry. 2015 Nov 16;21(47):16796-800. doi: 10.1002/chem.201503596. Epub 2015 Oct 5.
The dimethylamino (Me2N) group is arguably the most versatile functional group capable of highly efficient and site-selective directed aromatic functionalizations at the ortho-, meta-, and para-positions depending on reaction conditions. While the repertoire of Me2N-directed reactions is growing at a rapid pace, the lack of a general method to transform this group to other functionalities hampers its wider application in organic synthesis. Here we report nickel-catalyzed C-N borylations of aryl- and benzyl-dimethylamines that permit the conversion of a huge library of largely underutilized Me2N-containing organic molecules into various functional molecules by taking advantage of the wealth of existing C-B functionalization methods.
二甲基氨基（Me2N）基团可以说是最通用的官能团，根据反应条件，它能够在邻位、间位和对位进行高效且位点选择性的定向芳香族官能化反应。虽然Me2N定向反应的种类正在迅速增加，但缺乏将该基团转化为其他官能团的通用方法阻碍了其在有机合成中的更广泛应用。在此，我们报道了镍催化的芳基和苄基二甲基胺的C-N硼化反应，该反应利用大量现有的C-B官能化方法，可将大量未充分利用的含Me2N有机分子转化为各种功能分子。
