Costa, Dora C. S., da S. M. Forezi, Luana, Lessa, Milena D., Delarmelina, Maicon ![]() |
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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 |
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Date Type: | Publication |
Status: | Published |
Schools: | Chemistry 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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