Solvent-Directed Transition Metal-Free C-C Bond Cleavage by Azido-1,3,5-triazines and Their Stability-Reactivity Paradox

被引：3
|
作者：
Ma, Fulei [1 ]
Xie, Xiaoyu [1 ]
Li, Yuanheng [1 ]
Yan, Ziqiang [1 ]
Ma, Mingming [1 ]
机构：
[1] Univ Sci & Technol China, CAS Key Lab Soft Matter Chem, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 01期
基金：
中国国家自然科学基金;
关键词：
Aryl ketones - C-c bond cleavages - Carbon-carbon bond cleavage - DFT calculation - High reactivity - Regio-selective - Steric hindrances - Transition metal catalysts;
D O I：
10.1021/acs.joc.0c02342
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report a solvent-directed and regioselective carbon-carbon bond cleavage of aryl ketones by azido-1,3,5-triazines (ATs), which is typically completed within 10 min in DMSO at room temperature, without using transition metal catalysts. The cleavage is driven by the steric hindrance in the adducts of aryl ketones and ATs, which is substantiated by DFT calculation. Our recent results showed that ATs present high reactivity in solution and high stability in solid state. This "stability-reactivity paradox" has been explained in light of the molecular and crystal structures of ATs.
引用
收藏
页码：762 / 769
页数：8
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