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. 2021 Aug 16;27(46):11823-11826.
doi: 10.1002/chem.202101273. Epub 2021 Jul 7.

Nickel-Catalyzed Thiolation of Aryl Nitriles

Tristan Delcaillau  1 , Bill Morandi  1
Affiliations

Nickel-Catalyzed Thiolation of Aryl Nitriles

Tristan Delcaillau et al. Chemistry. .

Abstract

A nickel-catalyzed thiolation of aryl nitriles has been developed to access functionalized aryl thioethers. The ligand dcype (1,2-bis(dicyclohexylphosphino)ethane) as well as the base KOt Bu (potassium tert-butoxide) are essential to achieve this transformation. This scalable and practical process involves both a C-C bond activation and a C-S bond formation. Furthermore, this reaction shows a high functional-group tolerance and enables the late-stage functionalization of important molecules.

Keywords: catalysis; late-stage; nickel; nitrile; thioethers.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Context of the work.
Scheme 2
Scheme 2
Plausible mechanism.
See this image and copyright information in PMC

References

    1. Fleming F. F., Nat. Prod. Rep. 1999, 16, 597–606.
    1. A. Kleemann, J. Engel, B. Kutscher, D. Reichert, Pharmaceutical Substance: Synthesis, Patents and Applications of the Most Relevant AIPs, 5th edn.; Thieme: Stuttgart, 2008, pp. 1–1800.
    1. Rappoport Z., Chemistry of The Cyano Group; John Wiley & Sons: London, 1970, pp1-1044.
    1. None
    1. Kim K., Hong S. H., Adv. Synth. Catal. 2017, 359, 2345–2351;

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