Steric Engineering of Rotaxane Catalysts: Benefits and Limits of Using the Mechanical Bond in Catalyst Design

F. Robin Struth; Dennis Jansen; Noël Pairault; Marcel Schumacher; Florian Uteschil; Jürgen Linders; Christian Mayer; André H. Gröschel; Stephen M. Goldup; Jochen Niemeyer

doi:10.1002/chem.202402717

Steric Engineering of Rotaxane Catalysts: Benefits and Limits of Using the Mechanical Bond in Catalyst Design

F. Robin Struth, Dennis Jansen, Noël Pairault, Marcel Schumacher, Florian Uteschil, Jürgen Linders, Christian Mayer, André H. Gröschel, Stephen M. Goldup^*, Jochen Niemeyer^*

^*Corresponding author for this work

Chemistry

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Abstract

The mechanical bond is emerging as a novel design element in catalyst development. Here, we report a series of 1,1’‐binaphthyl‐2,2’‐diol (BINOL) based catalysts in which the number of interlocked macrocycles is varied. Unsurprisingly, the macrocycles have a profound steric influence on the catalytic performance of these molecules. However, in the enantioselective transformations examined, the macrocycles are detrimental to catalyst stereoselectivity whereas in lactide polymerization, they increase the molecular weight of the polymeric product.

Original language	English
Article number	e202402717
Journal	Chemistry: A European Journal
Early online date	14 Aug 2024
DOIs	https://doi.org/10.1002/chem.202402717
Publication status	E-pub ahead of print - 14 Aug 2024

Keywords

Enantioselective catalysis
Interlocked molecules
Lactide polymerization
BINOL
Rotaxanes

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StruthR2024StericFinal published version, 4.14 MBLicence: Creative Commons: Attribution-NonCommercial (CC BY-NC)

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Struth, F. R., Jansen, D., Pairault, N., Schumacher, M., Uteschil, F., Linders, J., Mayer, C., Gröschel, A. H., Goldup, S. M., & Niemeyer, J. (2024). Steric Engineering of Rotaxane Catalysts: Benefits and Limits of Using the Mechanical Bond in Catalyst Design. Chemistry: A European Journal, Article e202402717. Advance online publication. https://doi.org/10.1002/chem.202402717

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author = "Struth, {F. Robin} and Dennis Jansen and No{\"e}l Pairault and Marcel Schumacher and Florian Uteschil and J{\"u}rgen Linders and Christian Mayer and Gr{\"o}schel, {Andr{\'e} H.} and Goldup, {Stephen M.} and Jochen Niemeyer",

year = "2024",

month = aug,

day = "14",

doi = "10.1002/chem.202402717",

language = "English",

journal = "Chemistry: A European Journal",

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T1 - Steric Engineering of Rotaxane Catalysts

T2 - Benefits and Limits of Using the Mechanical Bond in Catalyst Design

AU - Struth, F. Robin

AU - Jansen, Dennis

AU - Pairault, Noël

AU - Schumacher, Marcel

AU - Uteschil, Florian

AU - Linders, Jürgen

AU - Mayer, Christian

AU - Gröschel, André H.

AU - Goldup, Stephen M.

AU - Niemeyer, Jochen

PY - 2024/8/14

Y1 - 2024/8/14

N2 - The mechanical bond is emerging as a novel design element in catalyst development. Here, we report a series of 1,1’‐binaphthyl‐2,2’‐diol (BINOL) based catalysts in which the number of interlocked macrocycles is varied. Unsurprisingly, the macrocycles have a profound steric influence on the catalytic performance of these molecules. However, in the enantioselective transformations examined, the macrocycles are detrimental to catalyst stereoselectivity whereas in lactide polymerization, they increase the molecular weight of the polymeric product.

AB - The mechanical bond is emerging as a novel design element in catalyst development. Here, we report a series of 1,1’‐binaphthyl‐2,2’‐diol (BINOL) based catalysts in which the number of interlocked macrocycles is varied. Unsurprisingly, the macrocycles have a profound steric influence on the catalytic performance of these molecules. However, in the enantioselective transformations examined, the macrocycles are detrimental to catalyst stereoselectivity whereas in lactide polymerization, they increase the molecular weight of the polymeric product.

KW - Enantioselective catalysis

KW - Interlocked molecules

KW - Lactide polymerization

KW - BINOL

KW - Rotaxanes

U2 - 10.1002/chem.202402717

DO - 10.1002/chem.202402717

M3 - Article

SN - 0947-6539

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

M1 - e202402717

ER -

Steric Engineering of Rotaxane Catalysts: Benefits and Limits of Using the Mechanical Bond in Catalyst Design

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