C-H⋅⋅⋅X-C bonds in alkyl halides drive reverse selectivities in confined spaces

Petroselli, Manuel; Chen, Yongqing; Zhao, Ming-Kai; Rebek, Julius; Yu, Yang

doi:10.1016/j.cclet.2022.107834

Cited by 8 publications

(2 citation statements)

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“…Substrate selectivity can vary considerably depending on the specific size and shape of the competing substrates under investigation. In particular, one difficult substrate selectivity to achieve is between substrates with basically identical electronic and steric properties in close proximity to the functional group that is transformed in the catalytic reaction, but that differ in size and shape in the rest of the molecular structure far away from the point where the reaction takes place [24] . In order to achieve this target, the catalyst needs to completely solvate the substrates to be able to show a certain level of substrate selectivity.…”

Section: Introductionmentioning

confidence: 99%

“…In particular, one difficult substrate selectivity to achieve is between substrates with basically identical electronic and steric properties in close proximity to the functional group that is transformed in the catalytic reaction, but that differ in size and shape in the rest of the molecular structure far away from the point where the reaction takes place. [24] In order to achieve this target, the catalyst needs to completely solvate the substrates to be able to show a certain level of substrate selectivity. This requires complex and extended molecular structures to ensure substrate recognition, which means time consuming synthesis of elaborate promoters.…”

Section: Introductionmentioning

confidence: 99%

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Substrate Selectivity Imparted by Self‐Assembled Molecular Containers and Catalysts

Lorenzetto,

Bordignon,

Munarin

et al. 2024

Chemistry A European J

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Recent trends in catalysis are devoted to mimicking some peculiar features of enzymes like site selectivity, through functional group recognition, and substrate selectivity, through recognition of the entire surface of the substrate. The latter is a specific feature of enzymes that is seldomly present in homogeneous catalysis. Supramolecular catalysis, thanks to the self‐assembly of simple subunits, enables the creation of cavities and surfaces whose confinement effects drive the preferential binding of a substrate among others with consequent substrate selectivity. The topic is an emerging field that exploits recognition phenomena to discriminate the reagents based on their size and shape. This review deals this cutting‐edge field of research covering examples of supramolecular self‐assembled molecular containers and catalysts operating in organic as well as aqueous media, with special emphasis for catalytic systems dealing with direct competitive experiments involving two or more substrates.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%