Hydride Reduction by a Sodium Hydride-Iodide Composite
作者:Pei Chui Too、Guo Hao Chan、Ya Lin Tnay、Hajime Hirao、Shunsuke Chiba
DOI:10.1002/anie.201600305
日期:2016.3.7
Sodium hydride (NaH) is widely used as a Brønsted base in chemical synthesis and reacts with various Brønsted acids, whereas it rarely behaves as a reducing reagent through delivery of the hydride to polar π electrophiles. This study presents a series of reduction reactions of nitriles, amides, and imines as enabled by NaH in the presence of LiI or NaI. This remarkably simple protocol endows NaH with
Continuous Flow Preparation of Benzylic Sodium Organometallics
作者:Johannes H. Harenberg、Rajasekar Reddy Annapureddy、Konstantin Karaghiosoff、Paul Knochel
DOI:10.1002/anie.202203807
日期:2022.7.25
A lateral sodiation of alkyl(hetero)arenes using on-demand generated (2-ethylhexyl)sodium in the presence of TMEDA is reported. Various electrophiles were used for trapping of the benzyl sodium species generated in continuous flow as well as in batch. The continuous flow metalation was scaled-up using an in-line quench. The method was used in the synthesis of several industrial relevant compounds.