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Nickel-Catalyzed Cyanation of Aryl Thioethers

Tristan Delcaillau, Adrian Woenckhaus-Alvarez and Bill Morandi*

*ETH Zürich, Vladimir-Prelog-Weg 3, HCI, 8093 Zürich, Switzerland, Email: bill.morandiorg.chem.ethz.ch

T. Delcaillau, A. Woenckhaus-Alvare, B. Morandi, Org. Lett., 2021, 23, 7018-7022.

DOI: 10.1021/acs.orglett.1c02285


Abstract

The combination of KOAc as base and dcype (1,2-bis(dicyclohexylphosphino)ethane) as ligand is essential for achieving a nickel-catalyzed cyanation of aryl thioethers efficiently. The reaction offers scalability, low catalyst and reagents loadings, and high functional group tolerance.


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proposed mechanism



Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

T. Delcaillau, P. Boehm, B. Morandi, J. Am. Chem. Soc., 2021, 143, 3628-3637.


Key Words

cyanations


ID: J54-Y2021