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  Nickel‐Catalyzed Inter‐ and Intramolecular Aryl Thioether Metathesis by Reversible Arylation

Delcaillau, T., Bismuto, A., Lian, Z., & Morandi, B. (2020). Nickel‐Catalyzed Inter‐ and Intramolecular Aryl Thioether Metathesis by Reversible Arylation. Angewandte Chemie, International Edition, 59(5), 2110-2114. doi:10.1002/anie.201910436.

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Genre: Journal Article

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 Creators:
Delcaillau, Tristan1, 2, Author              
Bismuto, Alessandro1, Author
Lian, Zhong2, Author              
Morandi, Bill1, 2, Author              
Affiliations:
1Laboratorium für Organische Chemie, ETH Zürich, Vladimir-Prelog-Weg 3, HCI, 8093 Zürich, Switzerland, ou_persistent22              
2Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040309              

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Free keywords: macrocycles; reaction mechanisms; metathesis; nickel; thioethers
 Abstract: A nickel‐catalyzed aryl thioether metathesis has been developed to access high‐value thioethers. 1,2‐Bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional‐group‐tolerant reaction. Furthermore, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring‐closing metathesis that does not involve alkene bonds. In‐depth organometallic studies support a reversible Ni0/NiII pathway to product formation. Overall, this work not only provides a more sustainable alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information that are highly relevant to the further development and application of unusual single‐bond metathesis reactions.

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Language(s): eng - English
 Dates: 2019-08-152019-12-122020-01-27
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201910436
 Degree: -

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Title: Angewandte Chemie, International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 59 (5) Sequence Number: - Start / End Page: 2110 - 2114 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851