Nitrenium Salts in Lewis Acid Catalysis
Nitrenium Salts in Lewis Acid Catalysis
复制标题
DOI：
10.1002/anie.201915547
复制
发表时间：
2020-01-07
影响因子：
16.6
通讯作者：
Goicoechea, Jose M.
中科院分区：
文献类型：
--
作者：
Mehta, Meera;Goicoechea, Jose M.
以氮原子为特征的分子化合物通常被认为是刘易斯碱，并被广泛用作配位化学中的供体配体或有机化学中的亲核试剂。相比之下，亲电的含氮化合物就罕见得多。氮鎓阳离子是一类新的氮基刘易斯酸，其反应活性在很大程度上尚未研究。在这项工作中，氮离子作为催化剂在五个有机转化进行了探索。这些反应是使用氮作为底物活化位点的刘易斯酸催化的第一个例子。此外，这些化合物易于从市售试剂中获得，并对水分表现出显著的稳定性，允许在不需要预处理溶剂的情况下进行台式转化。
Molecular compounds featuring nitrogen atoms are typically regarded as Lewis bases and are extensively employed as donor ligands in coordination chemistry or as nucleophiles in organic chemistry. By contrast, electrophilic nitrogen-containing compounds are much rarer. Nitrenium cations are a new family of nitrogen-based Lewis acids, the reactivity of which remains largely unexplored. In this work, nitrenium ions are explored as catalysts in five organic transformations. These reactions are the first examples of Lewis acid catalysis employing nitrogen as the site of substrate activation. Moreover, these compounds are readily accessed from commercially available reagents and exhibit remarkable stability toward moisture, allowing for benchtop transformations without the need to pretreat solvents.