期刊
CHEMISTRYSELECT
卷 7, 期 24, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.202201334
关键词
Cross-coupling; Heterocycles; Lawsone; Molecular Modeling; Pd(OAc)(2); PEG-400
资金
- CNPq [301873/2019-4, 306011/2020-4, 404587/2021-6]
- CAPES [001]
- FAPERJ [E-26/201.369/2021, E-26/203.191/2017, E-26/202.800/2017, E-26/010.101106/2018, SEI-260003/001178/2020, E-26/211.027/2019, E-26/200.870/2021, E-26/211.343/2021]
A stereoselective and base-free Heck coupling between 1,4-naphthoquinone and 1H-1,2,3-triazole derivatives was reported for the first time. This study demonstrates that the use of an additional base is unnecessary for the synthesis of naphthoquinone-triazole conjugates. The reaction mechanism and substituent effects were also discussed in this work.
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.
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