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One-pot preparation of hydroxylated potassium organotrifluoroborates and subsequent Jones oxidation to potassium organocarbonyltrifluoroborates |
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| Authors: | Dong-Su KimKrishnavenu Bolla Seokjoon LeeJungyeob Ham |
| Affiliation: | a Marine Chemomics Laboratory, Natural Products Research Center, Korea Institute of Science and Technology, Gangneung 210-340, South Korea b Department of Medicinal and Pharmaceutical Chemistry, University of Science & Technology, Daejeon 305-350, South Korea c College of Medicine, Kwandong University, Gangneung 210-701, South Korea |
| Abstract: | Alcohol-containing potassium organotrifluoroborates as starting reagents were prepared from their corresponding dibromobenzenes through a sequential one-pot reaction. The oxidation reactions of these substrates, which were carried out using 3.0 equiv of 8 N Jones reagent in acetone at 0 °C, provided a high yield of the desired carbonyl-functionalized compounds. In addition, the cross-coupling reactions of these organocarbonyltrifluoroborates were successfully performed in the presence of 3 mol % of Pd(PPh3)4 catalyst at 100 °C. |
| Keywords: | One-pot reaction Hydroxylated potassium organotrifluoroborate Jones oxidation Potassium organocarbonyltrifluoroborate Suzuki-Miyaura cross-coupling reaction |
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