Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters

• 作者: Changyu Huang Jinpeng Li Jiaquan Wang Qingshu Zheng Zhenhua Li Tao Tu
• 来源期刊: 中国科学：化学（英文版）
• 年，卷（期）: 2021,（1）
• 所属期刊栏目: ARTICLES
• 页码范围: 66-71
• 页数: 6页
• 语种: 英文

摘要

The amide C-N cleavage has drawn a broad interest in synthetic chemistry,biological process and pharmaceutical industry.Transition-metal,luxury ligand or excess base were always vital to the transformation.Here,we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base.The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments,density functional theory(DFT)calculations and kinetic studies.Besides broad substrate scopes and excellent functional groups tolerance,this base-catalyzed protocol com-plements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry.