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Chemistry A European J - 2024 - Winfrey - H2O B C6F5 3‐Catalyzed para‐Alkylation of Anilines with Alkenes Applied to.pdf (8.09 MB)

H2O ⋅ B(C6F5)3-Catalyzed para-Alkylation of Anilines with Alkenes Applied to Late-Stage Functionalization of Non-Steroidal Anti-Inflammatory Drugs

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Version 2 2024-02-12, 15:59
Version 1 2023-12-19, 12:21
journal contribution
posted on 2024-02-12, 15:59 authored by Laura Winfrey, Lei Yun, Ginevra Passeri, Kogularamanan Suntharalingam, Alexander Pulis

Anilines are core motifs in a variety of important molecules including medicines, materials and agrochemicals. We report a straightforward procedure that allows access to new chemical space of anilines via their para-C−H alkylation. The method utilizes commercially available catalytic H2O ⋅ B(C6F5)3 and is highly selective for para-C-alkylation (over N-alkylation and ortho-C-alkylation) of anilines, with a wide scope in both the aniline substrates and alkene coupling partners. Readily available alkenes are used, and include new classes of alkene for the first time. The mild reaction conditions have allowed the procedure to be applied to the late-stage-functionalization of non-steroidal anti-inflammatory drugs (NSAIDs), including fenamic acids and diclofenac. The formed novel NSAID derivatives display improved anti-inflammatory properties over the parent NSAID structure.

Funding

Royal Society. Grant Number: RGS\R1\191082

Stopped-Flow NMR Spectroscopy for the Physical and Life Sciences

Engineering and Physical Sciences Research Council

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Engineering and Physical Sciences Research Council. Grant Numbers: EP/Y00146X/1

History

Author affiliation

School of Chemistry, University of Leicester

Version

  • VoR (Version of Record)

Published in

Chemistry - A European Journal

Publisher

Wiley

issn

1521-3765

Copyright date

2024

Available date

2024-02-12

Language

en

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