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: https://orcid.org/0000-0002-8658-3897, Richards, Emma ORCID: https://orcid.org/0000-0001-6691-2377, Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667 and Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831 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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Abstract

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: http://creativecommons.org/licenses/by/4.0/
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
URI:	https://orca.cardiff.ac.uk/id/eprint/166513

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