Journal
TETRAHEDRON
Volume 76, Issue 47, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2020.131632
Keywords
Diazonium salts; Gomberg-Bachmann-Hey reaction; Copper catalysis; Mechanistic studies; C-H bond Activation
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Funding
- University of Torino
- Ministero dell'Universita e della Ricerca Scientifica
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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. (C) 2020 Elsevier Ltd. All rights reserved.
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