One-pot cross-coupling/C–H functionalization reactions: Quinoline as a substrate and ligand through N–Pd interaction
One-pot cross-coupling/C–H functionalization reactions: Quinoline as a substrate and ligand through N–Pd interaction
Herein, we report a one-pot process that marries mechanistically distinct, traditional cross-coupling reactions with C–H functionalization using the same precatalyst. The reactions proceed in yields of up to 95%, in air, and require no extraneous ligand. The reactions are thought to be facilitated by harnessing the substrate quinoline as an N-ligand, and evidence of the palladium–quinoline interaction is provided by 1H-15N HMBC NMR spectroscopy and X-ray crystallographic structures. Application of the methodology is demonstrated by the quick formation of fluorescent, π-extended frameworks.
2585-2596
Shanahan, Rachel M.
a7f95208-4c75-45b0-8818-5546e2864e54
Hickey, Aobha
efb76d47-5834-493b-837b-78933d3f2565
Bateman, Lorraine
eb63c89b-91cb-41bf-95d7-7b13d2863050
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
MvGlacken, Gerard P.
967b0ada-b968-46b3-bc6b-2f7d7c0d13fa
21 February 2020
Shanahan, Rachel M.
a7f95208-4c75-45b0-8818-5546e2864e54
Hickey, Aobha
efb76d47-5834-493b-837b-78933d3f2565
Bateman, Lorraine
eb63c89b-91cb-41bf-95d7-7b13d2863050
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
MvGlacken, Gerard P.
967b0ada-b968-46b3-bc6b-2f7d7c0d13fa
Shanahan, Rachel M., Hickey, Aobha, Bateman, Lorraine, Light, Mark E. and MvGlacken, Gerard P.
(2020)
One-pot cross-coupling/C–H functionalization reactions: Quinoline as a substrate and ligand through N–Pd interaction.
Journal of Organic Chemistry, 85 (4), .
(doi:10.1021/acs.joc.9b03321).
Abstract
Herein, we report a one-pot process that marries mechanistically distinct, traditional cross-coupling reactions with C–H functionalization using the same precatalyst. The reactions proceed in yields of up to 95%, in air, and require no extraneous ligand. The reactions are thought to be facilitated by harnessing the substrate quinoline as an N-ligand, and evidence of the palladium–quinoline interaction is provided by 1H-15N HMBC NMR spectroscopy and X-ray crystallographic structures. Application of the methodology is demonstrated by the quick formation of fluorescent, π-extended frameworks.
Text
McGlacken J Org Chem Clean Manuscript
- Accepted Manuscript
More information
Accepted/In Press date: 17 January 2020
e-pub ahead of print date: 23 January 2020
Published date: 21 February 2020
Additional Information:
Funding Information:
The authors would like to thank Dr. Trevor Carey, Prof John Sodeau, Dr. Peter Byrne, and Dr. Leticia Pardo for useful discussion. The authors acknowledge the Irish Research Council (IRC) and Science Foundation Ireland (SFI) (grant number SFI/12/IP/1315) and the Synthesis and Solid State Pharmaceutical Centre (SSPC) (SFI/12/RC/2275 and SFI/12/RC/2275_P2). The authors thank the European Cooperation in Science and Technology COST initiative for funding CA15106, C-H Activation in Organic Synthesis (CHAOS). This publication has emanated from research conducted with the financial support of SFI through a research infrastructure award for process flow spectroscopy (Prospect) under the grant number 15/RI/3221.
Publisher Copyright:
Copyright © 2020 American Chemical Society.
Identifiers
Local EPrints ID: 437981
URI: http://eprints.soton.ac.uk/id/eprint/437981
ISSN: 0022-3263
PURE UUID: 70c55adb-f7ba-4625-9021-6b049b60d802
Catalogue record
Date deposited: 25 Feb 2020 17:30
Last modified: 17 Mar 2024 05:20
Export record
Altmetrics
Contributors
Author:
Rachel M. Shanahan
Author:
Aobha Hickey
Author:
Lorraine Bateman
Author:
Gerard P. MvGlacken
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics
