Near quantitative synthesis of urea macrocycles enabled by bulky N-substituent

• DOI: 10.1038/s41467-021-21678-3
• Publication Date: 2021-03-10T11:03:12Z
• Authors: Yingfeng Yang; Hanze Ying; Zhixia Li; Jiang Wang; Yingying Chen; Binbin Luo; Danielle L. Gray; Andrew Ferguson; Qian Chen; Y. Z; Jianjun Cheng
• Keywords: Molar ratio

Abstract Macrocycles are unique molecular structures extensively used in the design of catalysts, therapeutics and supramolecular assemblies. Among all reactions reported to date, systems that can produce macrocycles high yield under reaction concentrations rare. Here we report use dynamic hindered urea bond (HUB) for construction with very efficiency. Mixing equal molar diisocyanate diamine leads formation discrete nearly quantitative yields concentration reactants. The bulky N - tert -butyl plays key roles facilitate macrocycles, providing not only kinetic control due cyclization-promoting cis C = O/ conformation, but also possibly thermodynamic stabilization weak association interactions. be readily removed by acid eliminate dynamicity HUB stabilize macrocycle structures.