Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/221463
Title: Exploring nickel-catalyzed organochalcogen synthesis via cross-coupling of benzonitrile and alkyl chalcogenols with computational tools
Author: Gómez-Mudarra, Francisco A.
Aullón López, Gabriel
Jover Modrego, Jesús
Keywords: Níquel
Oxidació
Reaccions d'addició
Nickel
Oxidation
Addition reactions
Issue Date: 1-Dec-2024
Publisher: Royal Society of Chemistry
Abstract: The preparation of organochalcogens has increased in recent times due to their promising biological activity properties. This work studies the reaction mechanism of a nickel(0)-catalyzed cross-coupling between benzonitrile and propanethiol to produce new C–S bonds by computational means. The proposed mechanism follows the classical oxidative addition/transmetalation/reductive elimination cross-coupling sequence, involving an unusual oxidative addition of a Ph–CN bond onto the active species. The computed catalytic cycle for thioether synthesis has been examined to determine whether the same protocol could be employed to build the analogous C–Se and C–Te bonds. The proposed mechanism for C–S coupling is validated by microkinetic modeling and shows a very good agreement with available experimental data. The extension of the proposed mechanism to C–Se and C–Te couplings indicates that these new reactions should be operative, although their reaction rates appear to be significantly slower.
Note: Versió postprint del document publicat a: https://doi.org/10.1039/D4OB01865F
It is part of: Organic & Biomolecular Chemistry, 2024, vol. 23, num.7, p. 1673-1682
URI: https://hdl.handle.net/2445/221463
Related resource: https://doi.org/10.1039/D4OB01865F
ISSN: 1477-0520
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)
Articles publicats en revistes (Institut de Química Teòrica i Computacional (IQTCUB))

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