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DOI: 10.1055/a-2331-2707
Palladium-Catalyzed Cyanations of Aryl Imidazolylsulfonates with K4[Fe(CN)6]: A Pragmatic Approach to Benzonitriles from Phenols
Authors
D.E.F. would like to thank the Max and Minnie Tomerlin Voelcker Fund for unrestricted funds to our laboratories at UTSA. The UTSA NMR and X-ray facilities are supported by the National Science Foundation (NSF) (CHE-1625963 and CHE-1920057).
Dedicated to Prof. Erick M. Carreira on the occasion of his 60th birthday.
Abstract
A general Pd-catalyzed approach for the conversion of phenols into benzonitriles via aryl imidazolylsulfonates with a non-toxic cyanide source, potassium ferrocyanide, has been developed. Salient features of this method include low palladium precatalyst loadings (as low as 1.0 mol% total Pd), mild reaction conditions, and environmentally benign by-products compared to other (pseudo)halide aryl electrophiles. The initial scope of the reaction on a range of phenolic precursors is demonstrated including a one-pot, two-step approach to convert phenols directly into benzonitriles.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2331-2707.
- Supporting Information (PDF)
Publication History
Received: 11 April 2024
Accepted after revision: 22 May 2024
Accepted Manuscript online:
22 May 2024
Article published online:
18 June 2024
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