Costa, Dora C. S., da S. M. Forezi, Luana, Lessa, Milena D., Delarmelina, Maicon  ORCID: https://orcid.org/0000-0002-6414-552X, Matuck, Beatriz V. A., Freitas, Maria Clara R., Ferreira, Vitor F., de C. Resende, Jackson A. L., de M. Carneiro, José Walkimar and de C. da Silva, Fernando
2022.
A stereoselective, base-free, palladium-catalyzed heck coupling between 3-halo-1,4-naphthoquinones and vinyl-1H-1,2,3-triazoles.
ChemistrySelect
7
(24)
, e202201334.
10.1002/slct.202201334
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Abstract
A stereoselective, base-free Heck coupling between 1,4-naphthoquinone and 1H-1,2,3-triazole derivatives was reported for the first time. This study shows that depending on the 1,4-naphthoquinone, the use of an additional base is unnecessary to produce the naphthoquinone-triazole conjugates. This is also the first example of a Heck coupling of these two cores without using a base as an additive. In this work, sixteen new naphthoquinone-triazole hybrids were stereoselectively synthetized in good to excellent yields. The reaction mechanism was discussed based on DFT CAM−B3LYP calculations. The first step is the coordination of the arene to the palladium catalyst to form a palladacycle intermediate. After reorganization in this intermediate, the double bond in the arene is restored to proceed with the coupling step and formation of the C−C bond in the rate determining step. The Kozuchi-Shaik span model was employed to rationalize substituent effects.
| Item Type: | Article |
|---|---|
| Date Type: | Publication |
| Status: | Published |
| Schools: | Schools > Chemistry Research Institutes & Centres > Cardiff Catalysis Institute (CCI) |
| Publisher: | Wiley |
| ISSN: | 2365-6549 |
| Date of First Compliant Deposit: | 1 September 2022 |
| Date of Acceptance: | 13 June 2022 |
| Last Modified: | 22 Nov 2024 19:45 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/152285 |
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