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Synlett 2020; 31(11): 1121-1125
DOI: 10.1055/s-0040-1707116
DOI: 10.1055/s-0040-1707116
letter
Efficient Pd-Catalyzed Hydrodehalogenation of o-Haloanilides in Water
This work was financially supported by the National Natural Science Foundation of China (Grant. No. 81560620), the Yunnan Provincial Science and Technology Department-Applied Basic Research Joint Special Funds of Yunnan University of Chinese Medicine (Grant. No. 2017FF117(-023)).
Weitere Informationen
Publikationsverlauf
Received: 28. Februar 2020
Accepted after revision: 19. April 2020
Publikationsdatum:
12. Mai 2020 (online)
◊ These authors contributed equally to this work
Abstract
In the present work, we have developed a practical methodology for the hydrodehalogenation of o-haloanilides using PdCl2 at 100 °C under mild conditions in water. The catalytic system could selectively dehalogenate both aryl chloride and aryl bromide and exhibit a broad functional group tolerance.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707116.
- Supporting Information
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References and Notes
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- 15 General Procedure for Hydrodehalogenation of o-Haloanilides To a stirred solution of o-haloanilide (1 mmol), PdCl2 (3.6 mg, 0.02 mmol), Et3N (202 mg, 2 mmol), and dppap (8.5 mg, 0.05 mmol) in water (5 mL) at 100 °C for 12 h. After completion of the reaction (indicated by TLC), the mixture was filtered, and the filtrate was extracted with EtOAc (2 × 5 mL). The organic layer was dried by anhydrous Na2SO4, concentrated in vacuo, and the residue was isolated by column chromatography (PE/EtOAc, 5:1) to afford the respective products. N-Phenylacetamide (2a) Prepared according to the general procedure from 1aa as a white solid (mp 111–113 °C); yield: 116 mg (86%). 1H NMR (400 MHz, CDCl3): δ = 8.34 (s, 1 H), 7.44 (d, J = 7.8 Hz, 2 H), 7.21 (t, J = 7.7 Hz, 2 H), 7.02 (t, J = 5.3 Hz, 1 H), 2.06 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 169.34, 138.04, 128.94, 124.44, 120.36, 24.33.