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Continuous-Flow Synthesis of Biaryls by Negishi Cross-Coupling of Fluoro- and Trifluoromethyl-Substituted (Hetero)arenes

Roesner, S and Buchwald, SL (2016) Continuous-Flow Synthesis of Biaryls by Negishi Cross-Coupling of Fluoro- and Trifluoromethyl-Substituted (Hetero)arenes. Angewandte Chemie - International Edition, 55 (35). pp. 10463-10467. ISSN 1433-7851

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A continuous-flow method for the regioselective arylation of fluoroarenes and fluoropyridines has been developed. The telescoped procedure reported here consists of a three-step metalation, zincation, and Negishi cross-coupling sequence, providing efficient access to a variety of functionalized 2-fluorobiaryl products. Precise temperature control of the metalation step, made possible by continuous-flow technology, allowed for the efficient preparation of the arylated products in high yields and short residence times. Additionally, several examples of the regioselective arylation of benzotrifluoride derivatives are also provided.

Item Type: Article
Additional Information: This is the peer reviewed version of the following article: Roesner, Stefan and Buchwald, Stephen L.. (2016) Continuous-flow synthesis of biaryls by negishi cross-coupling of fluoro- and trifluoromethyl-substituted (hetero)arenes. Angewandte Chemie International Edition, 55 (35). pp. 10463-10467 which has been published in final form at http://doi.org/10.1002/anie.201605584. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
Uncontrolled Keywords: biaryls; cross-coupling; flow chemistry; palladium; synthetic methods; 03 Chemical Sciences; Organic Chemistry
Subjects: R Medicine > RS Pharmacy and materia medica
Divisions: Pharmacy & Biomolecular Sciences
Publisher: Wiley
SWORD Depositor: A Symplectic
Date Deposited: 24 Apr 2024 12:45
Last Modified: 24 Apr 2024 12:45
DOI or ID number: 10.1002/anie.201605584
URI: https://researchonline.ljmu.ac.uk/id/eprint/23120
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