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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
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.
0022-3263
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
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), 2585-2596. (doi:10.1021/acs.joc.9b03321).

Record type: Article

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.

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McGlacken J Org Chem Clean Manuscript - Accepted Manuscript
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More information

Accepted/In Press date: 17 January 2020
e-pub ahead of print date: 23 January 2020
Published date: 21 February 2020

Identifiers

Local EPrints ID: 437981
URI: http://eprints.soton.ac.uk/id/eprint/437981
ISSN: 0022-3263
PURE UUID: 70c55adb-f7ba-4625-9021-6b049b60d802
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 25 Feb 2020 17:30
Last modified: 26 Nov 2021 05:56

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Contributors

Author: Rachel M. Shanahan
Author: Aobha Hickey
Author: Lorraine Bateman
Author: Mark E. Light ORCID iD
Author: Gerard P. MvGlacken

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