Zhang Yang, Xie Sheng, Yan Mingdi, Ramström Olof
Department of Chemistry, KTH-Royal Institute of Technology, Teknikringen 36, 10044, Stockholm, Sweden.
Department of Chemistry, University of Massachusetts Lowell, 1 University Ave., Lowell, MA, 01854, USA.
Chemistry. 2017 Sep 4;23(49):11908-11912. doi: 10.1002/chem.201702363. Epub 2017 Aug 9.
The dynamic exchange of enamines from secondary amines and enolizable aldehydes has been demonstrated in organic solvents. The enamine exchange with amines was efficiently catalyzed by Bi(OTf) and Sc(OTf) (2 mol %) and the equilibria (60 mm) could be attained within hours at room temperature. The formed dynamic covalent systems displayed high stabilities in basic environment with <2 % by-product formation within one week after complete equilibration. This study expands the scope of dynamic C-N bonds from imine chemistry to enamines, enabling further dynamic methodologies in exploration of this important class of structures in systems chemistry.
仲胺与可烯醇化醛之间烯胺的动态交换已在有机溶剂中得到证实。Bi(OTf)和Sc(OTf)（2 mol%）能有效催化烯胺与胺的交换，在室温下数小时内即可达到平衡（60 mM）。形成的动态共价体系在碱性环境中表现出高稳定性，完全平衡后一周内副产物生成量<2%。本研究将动态C-N键的范围从亚胺化学扩展到烯胺，为在体系化学中探索这一重要结构类别提供了更多动态方法。
