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Synlett 2023; 34(08): 943-947
DOI: 10.1055/a-1996-3244
DOI: 10.1055/a-1996-3244
letter
Palladium-Catalyzed Carbonyl-Retention Suzuki–Miyaura Coupling between N-Hydroxybenzotriazole Esters and Boronic Acids
Authors
We are grateful for the financial support provided by the National Natural Science Foundation of China (21901163) and Shanghai Municipal Education Commission (QD2019024).
Abstract
We have developed a palladium-catalyzed C–O bond activation of N-hydroxybenzotriazole esters, which represent a new type of electrophilic partner for Suzuki–Miyaura cross-coupling reactions to make various ketones. This reaction employed the cheap and commercially available PdCl2(MeCN)2/PCy3 as the catalyst and proceeded at 80 °C.
Key words
palladium catalysis - Suzuki–Miyaura coupling - C–O bond activation - activated esters - ketone synthesis - N-hydroxybenzotriazoleSupporting Information
- Supporting information for this article is
available online at https://doi.org/10.1055/a-1196-3244.
- Supporting Information (PDF)
Publication History
Received: 15 November 2022
Accepted after revision: 12 December 2022
Accepted Manuscript online:
12 December 2022
Article published online:
13 January 2023
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- 17 General Procedure for the Pd-Catalyzed Suzuki–Miyaura Coupling between AcOBt and Boronic Acid An oven-dried Schlenk tube was charged with a magnetic stir bar, PdCl2(MeCN)2 (2.59 mg, 0.02 mmol), PCy3 (5.61 mg, 0.04 mmol), O-acyl N-hydroxybenzotriazole (0.2 mmol), boronic acid (1.5 equiv), and K2CO3 (2.0 equiv) under air. Then the Schlenk tube was capped with a rubber septum and connected to a Schlenk line. The Schlenk tube was evacuated and back filled with N2 for three times before dioxane (2 mL) was added through a syringe. The perimeter of the septum was carefully sealed with parafilm. Next, the mixture was allowed for stirring at 80 °C in a metal sand bath for 12 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (5 mL), and the solvent was removed by a rotary evaporator. The crude product was purified by flash column chromatography (petroleum ether/ethyl acetate). Naphthalen-2-yl(phenyl)methanone (3l) The product was purified by flash column chromatography (petroleum ether/ethyl acetate = 200/1) as a white solid (30.4 mg, 66%), mp 82–84 °C. 1H NMR (400 MHz, CDCl3): δ = 8.27 (d, J = 1.3 Hz, 1 H), 7.98–7.84 (m, 6 H), 7.65–7.60 (m, 2 H), 7.59–7.49 (m, 3 H). 13C NMR (101 MHz, CDCl3): δ = 196.7, 137.9, 135.2, 134.8, 132.4, 132.2, 131.9, 130.1, 129.4, 128.3, 128.3, 128.3, 127.8, 126.8, 125.8. Furan-2-yl(phenyl)methanone (3m) The product was purified by flash column chromatography (petroleum ether/ethyl acetate = 300/1) as a white solid (14.9 mg, 43%), mp 43–45 °C. 1H NMR (400 MHz, CDCl3): δ = 8.02–7.93 (m, 2 H), 7.71 (d, J = 1.6 Hz, 1 H), 7.64–7.55 (m, 1 H), 7.49 (dd, J = 8.4, 7.0 Hz, 2 H), 7.23 (d, J = 3.6 Hz, 1 H), 6.59 (dd, J = 3.6, 1.7 Hz, 1 H). 13C NMR (101 MHz, CDCl3): δ = 182.5, 152.3, 147.1, 137.2, 132.6, 129.3, 128.4, 120.5, 112.2. Phenyl(thiophen-2-yl)methanone (3n) The product was purified by flash column chromatography (petroleum ether/ethyl acetate = 300/1) as a white solid (18.9 mg, 50%), mp 57–58 °C. 1H NMR (400 MHz, CDCl3): δ = 7.91–7.81 (m, 2 H), 7.72 (dd, J = 5.0, 1.2 Hz, 1 H), 7.65 (dd, J = 3.8, 1.2 Hz, 1 H), 7.62–7.56 (m, 1 H), 7.53–7.45 (m, 2 H), 7.16 (dd, J = 5.0, 3.8 Hz, 1 H). 13C NMR (101 MHz, CDCl3): δ = 188.2, 143.6, 138.1, 134.8, 134.2, 132.2, 129.1, 128.4, 127.9.
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