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

Yingfeng Yang, Hanze Ying, Zhixia Li, Jiang Wang, Yingying Chen, Binbin Luo, Danielle L. Gray, Andrew Ferguson, Qian Chen, Y. Z and Jianjun Cheng ()
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Yingfeng Yang: University of Illinois at Urbana-Champaign
Hanze Ying: University of Illinois at Urbana-Champaign
Zhixia Li: University of Illinois at Urbana-Champaign
Jiang Wang: Rice University
Yingying Chen: University of Illinois at Urbana-Champaign
Binbin Luo: University of Illinois at Urbana-Champaign
Danielle L. Gray: School of Chemical Sciences, University of Illinois at Urbana-Champaign
Andrew Ferguson: Pritzker School of Molecular Engineering, University of Chicago
Qian Chen: University of Illinois at Urbana-Champaign
Y. Z: University of Illinois at Urbana-Champaign
Jianjun Cheng: University of Illinois at Urbana-Champaign

Nature Communications, 2021, vol. 12, issue 1, 1-10

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

Date: 2021
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DOI: 10.1038/s41467-021-21678-3

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