2H-MoS2 is an appealing semiconductor because of its Earth-abundant nature, cheapness, and low toxicity. This material has shown promising catalytic activity for various energy-related processes, but its use in catalysis for C-C bond forming reactions towards useful organic compounds is still largely unexplored. The lack of examples in organic synthesis is mainly due to the intrinsic difficulties of using bulk 2H-MoS2 (e. g., low surface area), which implies the reliance on high catalytic loadings for obtaining acceptable yields. This makes the optimization process more expensive and tedious. Here, we report the development of a 2H-MoS2-mediated synthesis of valuable bis(indolyl)methane derivatives, using indoles and benzaldehydes as starting materials. Exploiting the Design of Experiments (DoE) method, we identified the critical parameters affecting the catalytic performance of commercial 2H-MoS2 powder and optimized the reaction conditions. Lastly, we demonstrated that the catalytic system has versatility and good tolerance towards functional group variations of the reagents.

DoE-Assisted Development of a 2H-MoS2-Catalyzed Approach for the Production of Indole Derivatives

Paolo Fornasiero;
2023

Abstract

2H-MoS2 is an appealing semiconductor because of its Earth-abundant nature, cheapness, and low toxicity. This material has shown promising catalytic activity for various energy-related processes, but its use in catalysis for C-C bond forming reactions towards useful organic compounds is still largely unexplored. The lack of examples in organic synthesis is mainly due to the intrinsic difficulties of using bulk 2H-MoS2 (e. g., low surface area), which implies the reliance on high catalytic loadings for obtaining acceptable yields. This makes the optimization process more expensive and tedious. Here, we report the development of a 2H-MoS2-mediated synthesis of valuable bis(indolyl)methane derivatives, using indoles and benzaldehydes as starting materials. Exploiting the Design of Experiments (DoE) method, we identified the critical parameters affecting the catalytic performance of commercial 2H-MoS2 powder and optimized the reaction conditions. Lastly, we demonstrated that the catalytic system has versatility and good tolerance towards functional group variations of the reagents.
2023
Istituto di Chimica dei Composti OrganoMetallici - ICCOM -
Inglese
16
21
e202300831
e202300831
8
https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cssc.202300831
Esperti anonimi
C-C coupling; heterogeneous catalysis; indole derivatives; molybdenum disulfide; synthetic methods
7
info:eu-repo/semantics/article
262
Gentile, Giuseppe; Morantginer, Marc; Cardo, Lucia; Melchionna, Michele; Fornasiero, Paolo; Prato, Maurizio; Filippini, Giacomo
01 Contributo su Rivista::01.01 Articolo in rivista
open
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Descrizione: DoE-Assisted Development of a 2H-MoS2-Catalyzed Approach for the Production of Indole Derivatives
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.14243/457591
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