当前位置: X-MOL 学术Chem › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
A room-temperature-stable electride and its reactivity: Reductive benzene/pyridine couplings and solvent-free Birch reductions
Chem ( IF 23.5 ) Pub Date : 2022-12-01 , DOI: 10.1016/j.chempr.2022.11.006
Nathan Davison, James A. Quirk, Floriana Tuna, David Collison, Claire L. McMullin, Hannes Michaels, George H. Morritt, Paul G. Waddell, Jamie A. Gould, Marina Freitag, James A. Dawson, Erli Lu

In this work, we report the synthesis of a room-temperature-stable electride (RoSE) reagent, namely K+(LiHMDS)e (1) (HMDS: 1,1,1,3,3,3-hexamethyldisilazide), from accessible starting materials (potassium metal and LiHMDS) via mechanochemical ball milling at 20 mmol scale. Despite its amorphous nature, the presence of anionic electrons in 1, key diagnostic criteria for an electride, was confirmed by both experimental and computational studies. Therefore, by definition, 1 is an electride. Utilizing its anionic electrons, electride reagent 1 exhibited a versatile reactivity profile that includes (1) mediation of C–H activation and C–C coupling of benzene and pyridine and (2) mediation of solvent-free Birch reduction. This work proves the concept of facile mechanochemical synthesis of a room-temperature-stable electride, and it introduces electride 1 to the synthetic chemistry community as a versatile reagent.



中文翻译:

室温稳定的电子及其反应性:还原苯/吡啶偶联和无溶剂 Birch 还原

在这项工作中,我们报告了室温稳定的电子化物 (RoSE) 试剂的合成,即 K + (LiHMDS)e ( 1 ) (HMDS: 1,1,1,3,3,3-hexamethyldisilazide),通过机械化学球磨以 20 mmol 规模从可获得的起始材料(钾金属和 LiHMDS)中提取。尽管具有无定形性质,但1中阴离子电子的存在(电子化物的关键诊断标准)已通过实验和计算研究得到证实。因此,根据定义,1是电子。利用其阴离子电子,电子试剂1表现出多种反应性特征,包括(1)介导苯和吡啶的 ​​C-H 活化和 C-C 偶联,以及(2)无溶剂 Birch 还原的介导。这项工作证明了室温稳定的电子化合物的简便机械化学合成概念,并将电子化合物1作为一种多功能试剂引入了合成化学界。

更新日期:2022-12-01
down
wechat
bug