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  A solid alkylation : highly recyclable, flow chemistry-ready, resin-supported thioimidazoliums alkylate sulfur-centered nucleophiles

Cataldo, V. A., Taimoory, S. M., Mohammadzadeh, S., Guterman, R., & Trant, J. (2022). A solid alkylation: highly recyclable, flow chemistry-ready, resin-supported thioimidazoliums alkylate sulfur-centered nucleophiles. European Journal of Organic Chemistry, 2022(35): e202200367. doi:10.1002/ejoc.202200367.

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Article.pdf (Publisher version), 888KB
 
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Cataldo, Vincenzo Alessandro1, Author           
Taimoory, S. Maryamdokht, Author
Mohammadzadeh, Sanam, Author
Guterman, Ryan1, Author           
Trant, John, Author
Affiliations:
1Ryan Guterman, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_2411691              

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Free keywords: alkylation; solid-support; protein methylation; thiol; mechanism
 Abstract: A series of readily regenerable thioimidazolium-based ionic liquids possessing the ability to transfer an alkyl group to a nucleophile are immobilized on crosslinked polystyrene beads. Different alkyl groups can be loaded onto the resin, highlighting the tunability of the material. The efficiency of these materials is demonstrated by their screening against a series of nucleophiles, showing a particular preference for thiols. Finally, these materials were evaluated for use under continuous flow conditions. The flexibility, ease of use, safety, and recyclability of these alkylating resins shows promise for their use in large scale and automated applications.

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Language(s): eng - English
 Dates: 2022-08-042022
 Publication Status: Published in print
 Pages: -
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 Table of Contents: -
 Rev. Type: -
 Identifiers: DOI: 10.1002/ejoc.202200367
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Title: European Journal of Organic Chemistry
  Other : Eur. J. Org. Chem.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : Wiley-VCH
Pages: - Volume / Issue: 2022 (35) Sequence Number: e202200367 Start / End Page: - Identifier: ISSN: 1434-193X