B(C6F5)3‐Catalysed Alkylation of Imidazo[1,2‐a]pyridines Using α,β‐Unsaturated Ketones-Reference-Cited by-同舟云学术

B(C₆F₅)₃‐Catalysed Alkylation of Imidazo[1,2‐a]pyridines Using α,β‐Unsaturated Ketones

Published:2024-02-21 Issue:12 Volume:27 Page:
ISSN:1434-193X
Container-title:European Journal of Organic Chemistry
language:en
Short-container-title:Eur J Org Chem

Author:

Alotaibi Nusaybah¹²,Babaahmadi Rasool¹,Pramanik Milan¹^ORCID,Das Sampurna¹,Kariuki Benson M.³,Richards Emma¹³,Wirth Thomas³^ORCID,Melen Rebecca L.¹^ORCID

Affiliation:

1. Cardiff Catalysis Institute School of Chemistry Cardiff University Translational Research Hub Maindy Road, Cathays Cardiff CF24 4HQ

2. Department of Chemistry King Faisal University College of Science P.O. Box 400 Al-Ahsa 31982 Saudi Arabia

3. School of Chemistry Cardiff University, Main Building Park Place Cardiff CF10 3AT

Abstract

AbstractFluorinated 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.

Funder

King Faisal University

Engineering and Physical Sciences Research Council

Cardiff University

Publisher

Wiley

Reference32 articles.

1. Imidazo[1,2-a]pyridines: Promising Drug Candidate for Antitumor Therapy

2. Imidazo[1,2-a]pyridine anthelmintic and antifungal agents

3. Synthesis and Antiviral Activity of Novel Erythrofuranosyl Imidazo[1,2-a]pyridine C-Nucleosides Constructed via Palladium Coupling of Iodoimidazo[1,2-a]pyridines and Dihydrofuran

4. Synthesis of Novel Imidazo[1,2-a]pyridines with Potent Activity against Herpesviruses

5. Novel Dicationic Imidazo[1,2-a]pyridines and 5,6,7,8-Tetrahydro-imidazo[1,2-a]pyridines as Antiprotozoal Agents

Cited by 1 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Transition-metal-free synthesis of triarylmethanes via Friedel-Crafts reactions of imidazo[1,2-a]pyridines with chlorohydrocarbon derivatives;Journal of Saudi Chemical Society;2024-07