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“Design of Experiments” as a Method to Optimize Dynamic Disulfide Assemblies: Cages and Functionalizable Macrocycles

Cyclophanes are a venerable class of macrocyclic and cage compounds that often contain unusual conformations, high strain, and unusual properties. However, synthesis of complex, functional derivatives remains difficult due to low functional group tolerance, high dilution, extreme reaction conditions...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2020-01, Vol.59 (4), p.1496-1500
Main Authors: Shear, Trevor A., Lin, Fuding, Zakharov, Lev N., Johnson, Darren W.
Format: Article
Language:English
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Summary:Cyclophanes are a venerable class of macrocyclic and cage compounds that often contain unusual conformations, high strain, and unusual properties. However, synthesis of complex, functional derivatives remains difficult due to low functional group tolerance, high dilution, extreme reaction conditions, and sometimes low yields using traditional stepwise synthetic methods. “Design of experiments” (DOE) is a method employed for the optimization of reaction conditions, and we showcase this approach to generate a dramatic increase in the yield of specific targets from two different self‐assembling systems. These examples demonstrate that DOE provides an additional tool in tuning self‐assembling, dynamic covalent systems. Eight new macrocycles with reactive functional handles were synthesized through metalloid‐assisted self‐assembly. “Design of experiments” was utilized to optimize reaction conditions for multiple systems to significantly increase the yield of a single, targeted macrocycle.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201912169