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B(C6F5)3-catalysed alkylation of imidazo[1,2-a]pyridines using α,β-unsaturated ketones

Alotaibi, Nusaybah, Babaahmadi, Rasool, Pramanik, Milan, Das, Sampurna, Kariuki, Benson M. ORCID:, Richards, Emma ORCID:, Wirth, Thomas ORCID: and Melen, Rebecca L. ORCID: 2024. B(C6F5)3-catalysed alkylation of imidazo[1,2-a]pyridines using α,β-unsaturated ketones. European Journal of Organic Chemistry 27 (12) , e202400022. 10.1002/ejoc.202400022

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Fluorinated triarylboranes have shown a breadth of reactivity as catalysts for organic transformations, particularly in carbon‐carbon bond forming reactions. Herein we report a facile, metal‐free synthetic route for the addition of 2‐phenylimidazo[1,2‐a]pyridines to α, β‐unsaturated ketones using B(C6F5)3 as a metal‐free catalyst. 25 examples of reactions leading to products in up to 97 % yield are reported. DFT studies show the role of B(C6F5)3 and hydrogen shuttling in the mechanism of this Michael alkylation.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Additional Information: License information from Publisher: LICENSE 1: URL:
Publisher: Wiley
ISSN: 1434-193X
Funders: EPSRC, Saudi Ministry of Education, King Faisal University, Royal Society for an International Newton Fellowship, Cardiff University
Date of First Compliant Deposit: 23 February 2024
Date of Acceptance: 2 February 2024
Last Modified: 16 Apr 2024 15:28

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