Valentin Magné
Synthesis of air‐stable, odorless thiophenol surrogates via Ni‐Catalyzed C−S cross‐coupling
Magné, Valentin; Ball, Liam T.
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
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 | Jun 4, 2020 |
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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