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Cross-Coupling of Chloro(hetero)arenes with Thiolates Employing a Ni(0)-Precatalyst

Paul H. Gehrtz, Valentin Geiger, Tanno Schmidt, Laura Sršan, Ivana Fleischer*

*Institute of Organic Chemistry, Faculty of Science and Mathematics, Eberhard-Karls University Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany, Email:

P. H. Gehrtz, V. Geiger, T. Schmidt, L. Sršan, I. Fleischer, Org. Lett., 2019, 21, 50-55.

DOI: 10.1021/acs.orglett.8b03476

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Air-stable defined Ni precatalysts enable a general and efficient coupling of challenging aryl chlorides and in situ generated aliphatic and aromatic thiolates at unprecedented moderate catalyst loadings and reaction temperatures. The reaction tolerates various functional groups and heterocyclic motifs. Depending on reaction conditions, aryl thiols can selectively undergo C-S or C-C couplings.

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A fine optimized version of this reaction converts also tertiary thiols and works without any organometallic base. DOI: 10.33774/chemrxiv-2021-tgvjk

Valentin Geiger, December 6th, 2021

Key Words

aryl sulfides

ID: J54-Y2019