Is Cu(<scp>iii</scp>) a necessary intermediate in Cu-mediated coupling reactions? A mechanistic point of view

Li, Shi-Jun; Lan, Yu

doi:10.1039/d0cc01946a

Cited by 54 publications

(28 citation statements)

References 77 publications

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“…Based on these findings and previous reports, 32,34,35 a plausible mechanism is proposed as presented in Scheme 5. DMF is first converted into the iminium ion A in the presence of O 2 and Cu(I), 32 and a nucleophilic addition reaction of iminium ion A with 1a generates B followed by elimination of dimethylamine.…”

Section: Feature Synthesissupporting

confidence: 66%

Copper-Catalyzed Oxidative Cyclization of 2-Aminobenzamide Derivatives: Efficient Syntheses of Quinazolinones and Indazolones

et al. 2021

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We herein promote a simple copper-catalyzed assembly to formulate quinazoline and indazolone derivatives in a single protocol manner. These transformations are based on that DMF can serve as reaction solvents and one carbon synthon for the construction of heterocyclic ring. Moreover, this protocol features with base and Bronsted acid free, environmentally benign, broad synthetic scope and scalability is demonstrated.

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Section: Feature Synthesissupporting

confidence: 66%

Copper-Catalyzed Oxidative Cyclization of 2-Aminobenzamide Derivatives: Efficient Syntheses of Quinazolinones and Indazolones

et al. 2021

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“…However, mechanisms involving radical oxidation to produce Cu(II) intermediates seem to operate in a significant number of reactions, and Cu(II) intermediates have been invoked in several mechanistic proposals for the Ullmann reaction. 2 , 7 , 8 …”

Section: Introductionmentioning

confidence: 99%

Transmetalation Reactions Triggered by Electron Transfer between Organocopper Complexes

et al. 2021

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[Cu(bipy)(C 6 F 5 )] reacts with most aryl iodides to form heterobiphenyls by cross-coupling, but when Rf–I is used (Rf = 3,5-dicholoro-2,4,6-trifluorophenyl), homocoupling products are also formed. Kinetic studies suggest that, for the homocoupling reaction, a mechanism based on transmetalation from [Cu(bipy)(C 6 F 5 )] to Cu(III) intermediates formed in the oxidative addition step is at work. Density functional theory calculations show that the interaction between these Cu(III) species and the starting Cu(I) complex involves a Cu(I)–Cu(III) electron transfer concerted with the formation of an iodine bridge between the metals and that a fast transmetalation takes place in a dimer in a triplet state between two Cu(II) units.

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“…S4, S6, ESI †), to be similar to that of the reactions catalyzed by [Fe1]. [Fe2] combines with the CQC double bond 26,27 of a molecule of 1R to form 2PC/2PC 0 , calculated to have relative free energy values of 8.5/14.5 kcal mol À1 . Different pathways exist in the combination of 2PC/2PC 0 with another 1R.…”

mentioning

confidence: 65%

[2+2] Cycloaddition or β-hydrogen elimination?—a DFT study of the reactions of propylene catalyzed by (PDI)Fe-metallacycle

et al. 2022

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Is Cu(iii) a necessary intermediate in Cu-mediated coupling reactions? A mechanistic point of view

Abstract: The different pathways have been summarized to disclose the key intermediate in copper-mediated coupling reactions.

Cited by 54 publications

References 77 publications

Copper-Catalyzed Oxidative Cyclization of 2-Aminobenzamide Derivatives: Efficient Syntheses of Quinazolinones and Indazolones

Copper-Catalyzed Oxidative Cyclization of 2-Aminobenzamide Derivatives: Efficient Syntheses of Quinazolinones and Indazolones

Transmetalation Reactions Triggered by Electron Transfer between Organocopper Complexes

[2+2] Cycloaddition or β-hydrogen elimination?—a DFT study of the reactions of propylene catalyzed by (PDI)Fe-metallacycle

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