Issue 31, 2019
From the journal:

RSC Advances

Synthesis of 3-aryl-2-phosphinoimidazo[1,2-a]pyridine ligands for use in palladium-catalyzed cross-coupling reactions†

Ryan Q. Tran,a   Seth A. Jacoby,a   Kaitlyn E. Roberts,a   William A. Swann,a   Nekoda W. Harris,a   Long P. Dinh, ORCID logo a   Emily L. Denisona  and  Larry Yet ORCID logo *a  

* Corresponding authors

a University of South Alabama, Department of Chemistry, Mobile, AL 36618, USA
E-mail: lyet@southalabama.edu

Abstract

3-Aryl-2-phosphinoimidazo[1,2-a]pyridine ligands were synthesized from 2-aminopyridine via two complementary routes. The first synthetic route involves the copper-catalyzed iodine-mediated cyclizations of 2-aminopyridine with arylacetylenes followed by palladium-catalyzed cross-coupling reactions with phosphines. The second synthetic route requires the preparation of 2,3-diiodoimidazo[1,2-a]pyridine or 2-iodo-3-bromoimidazo[1,2-a]pyridine from 2-aminopyridine followed by palladium-catalyzed Suzuki/phosphination or a phosphination/Suzuki cross-coupling reactions sequence, respectively. Preliminary model studies on the Suzuki synthesis of sterically-hindered biaryl and Buchwald–Hartwig amination compounds are presented with these ligands.

Graphical abstract: Synthesis of 3-aryl-2-phosphinoimidazo[1,2-a]pyridine ligands for use in palladium-catalyzed cross-coupling reactions

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Article information

DOI
https://doi.org/10.1039/C9RA02200G
Article type
Paper
Submitted
21 Mar 2019
Accepted
17 May 2019
First published
05 Jun 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 17778-17782

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Synthesis of 3-aryl-2-phosphinoimidazo[1,2-a]pyridine ligands for use in palladium-catalyzed cross-coupling reactions

R. Q. Tran, S. A. Jacoby, K. E. Roberts, W. A. Swann, Nekoda W. Harris, L. P. Dinh, E. L. Denison and L. Yet, RSC Adv., 2019, 9, 17778 DOI: 10.1039/C9RA02200G

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