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CC BY-ND-NC 4.0 · Synlett 2019; 30(14): 1673-1678
DOI: 10.1055/s-0039-1690110
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Activation of Quinolines by Cationic Chalcogen Bond Donors

P. Wonner
,
T. Steinke
,
S. M. Huber  ∗
This project has received funding from the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation programme (638337).
Further Information

Publication History

Received: 25 April 2019

Accepted after revision: 17 June 2019

Publication Date:
09 August 2019 (online)

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§ Both authors contributed equally

Published as part of the Cluster Organosulfur and Organoselenium Compounds in Catalysis

Abstract

The application of already established as well as novel selenium- and sulfur-based cationic chalcogen bond donors in the catalytic activation of quinoline derivatives is presented. In the presence of selected catalysts, rate accelerations of up to 2300 compared to virtually inactive reference compounds are observed. The catalyst loading can be reduced to 1 mol% while still achieving nearly full conversion for electron-poor and electron-rich quinolines. Contrary to expectations, preorganized catalysts were less active than the more flexible variants.

Key words

chalcogen bonding - Lewis acids - organocatalysis - noncovalent interactions - intermolecular interactions - chalcogens - reduction

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690110.
  • Supporting Information
 

  • References and Notes

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