Gomberg-Bachmann-Hey reactions were carried out in the presence of copper as a catalyst and gave rise to biaryls or heterobiaryls in good yields and in mild reaction conditions. A computational study of some key points of the reaction was performed. The results are coherent with the experimental data and confirm some aspects of the mechanism. The reaction free energies for the reduction in benzene by CuI of a set of 40 (hetero)arenediazonium tetrafluoroborates were calculated. Both the experiments and the calculations showed that in the coupling with substituted solvents (toluene, bromobenzene, nitrobenzene and anisole) the binding to the ortho position was always favoured

Copper catalysed Gomberg-Bachmann-Hey reactions of arenediazonium tetrafluoroborates and heteroarenediazonium obenzenedisulfonimides. Synthetic and mechanistic aspects

Achille Antenucci
Co-last
;
Margherita Barbero
Co-last
;
Stefano Dughera
Co-first
;
Giovanni Ghigo
Co-first
2020-01-01

Abstract

Gomberg-Bachmann-Hey reactions were carried out in the presence of copper as a catalyst and gave rise to biaryls or heterobiaryls in good yields and in mild reaction conditions. A computational study of some key points of the reaction was performed. The results are coherent with the experimental data and confirm some aspects of the mechanism. The reaction free energies for the reduction in benzene by CuI of a set of 40 (hetero)arenediazonium tetrafluoroborates were calculated. Both the experiments and the calculations showed that in the coupling with substituted solvents (toluene, bromobenzene, nitrobenzene and anisole) the binding to the ortho position was always favoured
2020
76
131632
1
10
https://www.sciencedirect.com/search?qs=131632&pub=Tetrahedron&cid=271372
Diazonium salts Gomberg-Bachmann-Hey reaction Copper catalysis Mechanistic studies CeH bond Activation
Achille Antenucci, Margherita Barbero, Stefano Dughera*, Giovanni Ghigo**
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/1762708
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