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Structural and electronic control of 1‐(2‐pyridyl)benzotriazole bidentate ligand in copper chemistry with application to catalysis in the A3 coupling reaction

Structural and electronic control of 1‐(2‐pyridyl)benzotriazole bidentate ligand in copper chemistry with application to catalysis in the A3 coupling reaction

Sampani, Stavroula I., Zdorichenko, Victor, Devonport, Jack, Rossini, Gioia, Leech, Matthew C., Lam, Kevin ORCID: 0000-0003-1481-9212, Cox, Brian, Abdul-Sada, Alaa, Vargas, Alfredo and Kostakis, George E. (2020) Structural and electronic control of 1‐(2‐pyridyl)benzotriazole bidentate ligand in copper chemistry with application to catalysis in the A3 coupling reaction. Chemistry - A European Journal, 27 (13). pp. 4394-4400. ISSN 0947-6539 (Print), 1521-3765 (Online) (doi:https://doi.org/10.1002/chem.202004781)

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Abstract

The 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.

Item Type: Article
Uncontrolled Keywords: complexes, electrochemistry, A3 coupling
Subjects: Q Science > Q Science (General)
Faculty / Department / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > School of Science (SCI)
Last Modified: 27 Jul 2021 07:44
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
Selected for GREAT 2019: None
Selected for REF2021: None
URI: http://gala.gre.ac.uk/id/eprint/30576

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