Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2022, Issue 26, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200056
Keywords
Cyclophanes; Dynamic covalent chemistry; Macrocycles; Self-assembly; Supramolecular chemistry
Categories
Funding
- US National Science Foundation (NSF) [CHE-2003928]
- NSF Graduate Research Fellowship Program [1309047]
- NSF [CHE-1625529]
- Bradshaw and Holzapfel Research Professorship in Transformational Science and Mathematics
- U.S. Department of Energy by Lawrence Livermore National Laboratory [DE-AC52-07NA27344]
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Cyclophanes are compounds with unique properties, but their synthesis can be challenging. This study presents a metalloid-directed self-assembly method for synthesizing disulfide and thioether assemblies, and demonstrates its applicability to macrocycles and diverse cage structures.
Cyclophanes are a fundamentally interesting class of compounds that host a wide range of unique and emergent properties. However, synthesis of complex and/or functionalized cyclophanes can often suffer from harsh reaction conditions, long reaction times, and sometimes low yields using stepwise methods. We have previously reported an efficient, high-yielding, metalloid-directed self-assembly method to prepare disulfide, thioether, and hydrocarbon cyclophanes and cages that feature mercaptomethyl-arenes as starting materials. Herein, we report the synthesis of 21 new disulfide and thioether assemblies that expand this high yielding self-assembly method to a wide breadth of macrocycles and cages with diverse structures. Remarkably, the high-yielding, efficient syntheses still proceed under dynamic covalent control using electron-deficient, heteroaryl, cycloalkyl, spiro, and even short alkenyl/alkynyl substrates.
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