Reductive Cleavage of Unactivated Carbon-Cyano Bonds under Ammonia-Free Birch Conditions
Reductive Cleavage of Unactivated Carbon-Cyano Bonds under Ammonia-Free Birch Conditions
复制标题
无氨桦木条件下未活性碳-氰基键的还原裂解
DOI：
10.1021/acs.joc.9b02028
复制
发表时间：
2019-12-20
影响因子：
3.6
通讯作者：
An, Jie
中科院分区：
文献类型：
--
作者：
Ding, Yuxuan;Luo, Shihui;An, Jie
使用 Na/15-crown-5/H2O 在单电子转移条件下实现了脂肪腈中未活化碳-氰基键还原裂解的通用方案。电子由来自实验室稳定的钠分散体和可回收的 15-crown-5 的电子化合物提供。 H2O提供质子源并抑制芳香族部分的还原。与传统Birch条件下生成的Na/NH3电子化合物体系相比，这种无氨电子化合物体系更加实用，并且对多种脂肪腈的脱氰化具有更好的反应活性和化学选择性。
A general protocol for the reductive cleavage of unactivated carbon-cyano bonds in aliphatic nitriles has been achieved under single-electron-transfer conditions using Na/15-crown-5/H2O. Electron is supplied by the electride derived from bench-stable sodium dispersions and recoverable 15-crown-5. H2O provides the proton source and suppresses the reduction of aromatic moieties. Compared with the Na/NH3 electride system generated under traditional Birch conditions, this ammonia-free electride system is more practical and features better reactivity and chemoselectivity for the decyanations of a broad range of aliphatic nitriles.