manuscript.pdf (1010.95 kB)
Structural and electronic control of the bidentate 1-(2-pyridyl)benzotriazole ligand in copper chemistry with application to catalysis in the A3 coupling reaction
journal contribution
posted on 2023-06-09, 22:25 authored by Stavroula Sampani, Victor Zdorichenko, Jack Devonport, Gioia Rossini, Matthew C Leech, Kevin Lam, Brian Cox, Alaa Abdul-Sada, Alfredo VargasAlfredo Vargas, George KostakisGeorge KostakisThe hybrid bidentate 1-(2-pyridyl)benzotriazole (pyb) ligand was introduced into 3d transition metal catalysis. Specifically, [CuII(OTf)2(pyb)2]·2?CH3CN (1) enables the synthesis of a wide range of propargylamines by the A3 coupling reaction at room temperature in the absence of additives. Experimental and high-level theoretical calculations suggest that the bridging N atom of the ligand imposes exclusive trans coordination at Cu and allows ligand rotation, while the N atom of the pyridine group modulates charge distribution and flux, and thus orchestrates structural and electronic precatalyst control permitting alkyne binding with simultaneous activation of the C-H bond via a transient CuI species.
History
Publication status
- Published
File Version
- Accepted version
Journal
Chemistry - A European JournalISSN
0947-6539Publisher
WileyExternal DOI
Issue
13Volume
27Page range
4394-4400Department affiliated with
- Chemistry Publications
Full text available
- Yes
Peer reviewed?
- Yes
Legacy Posted Date
2020-12-10First Open Access (FOA) Date
2021-12-10First Compliant Deposit (FCD) Date
2020-12-10Usage metrics
Categories
No categories selectedKeywords
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC