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Nickel-Catalyzed Inter- and Intramolecular Carbon-Sulfur Bond Metathesis by Reversible Arylation

preprint
submitted on 22.05.2019 and posted on 24.05.2019 by Tristan Delcaillau, Alessandro Bismuto, Zhong Lian, Bill Morandi
A nickel-catalyzed carbon-sulfur bond 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. Further, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis which does not involve alkene bonds. In-depth organometallic studies support a reversible Ni(0)-Ni(II) pathway to product formation. Overall, this work does not only disclose a more sustainable and more functional group tolerant alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information which are highly relevant to the further development and application of unusual single bond metathesis reactions.

Funding

ERC (ShuttleCat, Project ID : 757608)

Carlsberg Foundation

Max-Planck-Society

ETH Zürich

History

Email Address of Submitting Author

morandib@ethz.ch

Institution

ETH Zürich

Country

Switzerland

ORCID For Submitting Author

0000-0003-3968-1424

Declaration of Conflict of Interest

A patent application for C‒S metathesis has been filed (WO2018162364)

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