Cation-controlled chemoselective synthesis of N -aroylureas and imides via amidation of N -Boc arylamides
Cation-controlled chemoselective synthesis of N -aroylureas and imides via amidation of N -Boc arylamides
复制标题
通过 N-Boc 芳酰胺的酰胺化，阳离子控制化学选择性合成 N-芳酰脲和酰亚胺
DOI：
10.1039/d3qo00352c
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发表时间：
2023
影响因子：
5.4
通讯作者：
Li, Jie
中科院分区：
文献类型：
--
作者：
Wang, Jiamin;Shuai, Sujuan;Gan, Lishe;Luo, Yongxin;Jin, Huimin;Chen, Lingfeng;Zou, Dong;Liang, Guang;Walsh, Patrick J.;Li, Jie
在本研究中，第一个高化学选择性酰胺化的Boc和酰胺基团的N-R-N-Boc芳基酰胺是先进的。这种实用且操作简单的方法能够在不添加过渡金属的情况下以良好至优异的产率制备N-芳酰脲或酰亚胺。碱的选择在控制不等价羰基的反应性方面起着重要作用。观察到的Boc基团的酰胺化与芳基酰胺，ArCONH 2，当受到KOtBu，而酰亚胺与LiOH产生。密度泛函理论的研究，探讨分歧的机制。预计这些化学选择性方法将引起合成和药物化学界的兴趣。
In this study, the first highly chemoselective amidation of Boc and amide groups of N-R-N-Boc arylamides is advanced. This practical and operationally-simple method enables the preparation of either N-aroylureas or imides in good to excellent yields without addition of transition metals. The choice of base plays a significant role in controlling the reactivity of the inequivalent carbonyl groups. The amidation of the Boc group was observed with arylamides, ArCONH2, when subjected to KOtBu while imides were produced with LiOH. DFT studies are employed to explore the divergent mechanisms. It is anticipated that these chemoselective methods will be of interest to the synthetic and medicinal chemistry communities.