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Synthesis of air‐stable, odorless thiophenol surrogates via Ni‐Catalyzed C−S cross‐coupling

Magné, Valentin; Ball, Liam T.

Synthesis of air‐stable, odorless thiophenol surrogates via Ni‐Catalyzed C−S cross‐coupling Thumbnail


Authors

Valentin Magné

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LIAM BALL Liam.Ball@nottingham.ac.uk
Associate Professor



Abstract

Thiophenols are versatile synthetic intermediates whose practical appeal is marred by their air sensitivity, toxicity and extreme malodor. Herein we report an efficient catalytic method for the preparation of S-aryl isothiouronium salts, and demonstrate that these air-stable, odorless solids serve as user-friendly sources of thiophenols in synthesis. Diverse isothiouronium salts featuring synthetically useful functionality are readily accessible via nickelcatalyzed C-S cross-coupling of (hetero)aryl iodides and thiourea. Convenient, chromatography-free isolation of these salts is achieved via precipitation, allowing the methodology to be translated directly to large scales. Thiophenols are liberated from the corresponding isothiouronium salts upon treatment with a weak base, enabling an in situ release / S-functionalization strategy that entirely negates the need to isolate, purify or manipulate these noxious reagents

Citation

Magné, V., & Ball, L. T. (2019). Synthesis of air‐stable, odorless thiophenol surrogates via Ni‐Catalyzed C−S cross‐coupling. Chemistry - A European Journal, 25(37), 8903-8910. https://doi.org/10.1002/chem.201901874

Journal Article Type Article
Acceptance Date May 8, 2019
Online Publication Date Jun 3, 2019
Publication Date Jun 3, 2019
Deposit Date Jun 3, 2019
Publicly Available Date Mar 28, 2024
Journal Chemistry – A European Journal
Print ISSN 0947-6539
Electronic ISSN 1521-3765
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 25
Issue 37
Pages 8903-8910
DOI https://doi.org/10.1002/chem.201901874
Keywords General Chemistry
Public URL https://nottingham-repository.worktribe.com/output/2130698
Publisher URL https://onlinelibrary.wiley.com/doi/full/10.1002/chem.201901874
Additional Information This is the peer reviewed version of the following article: Magné, V. and Ball, L. T. (2019), Synthesis of Air‐stable, Odorless Thiophenol Surrogates via Ni‐Catalyzed C−S Cross‐Coupling. Chem. Eur. J., which has been published in final form at doi:10.1002/chem.201901874. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.

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