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A stereoselective, base-free, palladium-catalyzed heck coupling between 3-halo-1,4-naphthoquinones and vinyl-1H-1,2,3-triazoles

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: 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: 28 Nov 2022 06:38
URI: https://orca.cardiff.ac.uk/id/eprint/152285

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