Palladium(II)-catalyzed synthesis of 2H,3'H‑spiro[benzofuran-3,2'-naphthoquinones]
- Author
- Pieter Claes (UGent) , Jan Jacobs (UGent) , Bart Kesteleyn, Tuyen Nguyen Van and Norbert De Kimpe (UGent)
- Organization
- Abstract
- 2H,3′H-Spiro[benzofuran-3,2′-naphthoquinones], constituting a new spiroheterocyclic skeleton, were synthesized starting from 2-aryloxymethyl-1,4-naphthoquinones by means of a palladium(II)-catalyzed reaction, which is a new spirocyclic transformation. Under optimal conditions, i.e. 10 mol % of palladium(II) acetate, 15 mol % of 3,5-dichloropyridine, and 5 mol % of trifluoroacetic acid in acetic acid at 110 °C, various 2H,3′H-spiro[benzofuran-3,2′-naphthoquinones] were synthesized in yields strongly dependent on the substitution pattern of the aryloxy group. Unsubstituted or ortho-substituted 2-aryloxymethyl-1,4-quinones were found to rearrange toward the corresponding 2-(4-hydroxyaryl)-1,4-quinones upon treatment with trifluoroacetic acid.
- Keywords
- palladium(II)-catalysis, 4-quinones, spiroquinones, 2-Aryloxymethyl-1, ARYLATIONS, DERIVATIVES, CATALYST, QUINONES, 2 NAPHTHOQUINONE ANTIBIOTICS
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-4128481
- MLA
- Claes, Pieter, et al. “Palladium(II)-Catalyzed Synthesis of 2H,3’H‑spiro[Benzofuran-3,2’-Naphthoquinones].” JOURNAL OF ORGANIC CHEMISTRY, vol. 78, no. 17, 2013, pp. 8330–39, doi:10.1021/jo400852z.
- APA
- Claes, P., Jacobs, J., Kesteleyn, B., Van, T. N., & De Kimpe, N. (2013). Palladium(II)-catalyzed synthesis of 2H,3’H‑spiro[benzofuran-3,2’-naphthoquinones]. JOURNAL OF ORGANIC CHEMISTRY, 78(17), 8330–8339. https://doi.org/10.1021/jo400852z
- Chicago author-date
- Claes, Pieter, Jan Jacobs, Bart Kesteleyn, Tuyen Nguyen Van, and Norbert De Kimpe. 2013. “Palladium(II)-Catalyzed Synthesis of 2H,3’H‑spiro[Benzofuran-3,2’-Naphthoquinones].” JOURNAL OF ORGANIC CHEMISTRY 78 (17): 8330–39. https://doi.org/10.1021/jo400852z.
- Chicago author-date (all authors)
- Claes, Pieter, Jan Jacobs, Bart Kesteleyn, Tuyen Nguyen Van, and Norbert De Kimpe. 2013. “Palladium(II)-Catalyzed Synthesis of 2H,3’H‑spiro[Benzofuran-3,2’-Naphthoquinones].” JOURNAL OF ORGANIC CHEMISTRY 78 (17): 8330–8339. doi:10.1021/jo400852z.
- Vancouver
- 1.Claes P, Jacobs J, Kesteleyn B, Van TN, De Kimpe N. Palladium(II)-catalyzed synthesis of 2H,3’H‑spiro[benzofuran-3,2’-naphthoquinones]. JOURNAL OF ORGANIC CHEMISTRY. 2013;78(17):8330–9.
- IEEE
- [1]P. Claes, J. Jacobs, B. Kesteleyn, T. N. Van, and N. De Kimpe, “Palladium(II)-catalyzed synthesis of 2H,3’H‑spiro[benzofuran-3,2’-naphthoquinones],” JOURNAL OF ORGANIC CHEMISTRY, vol. 78, no. 17, pp. 8330–8339, 2013.
@article{4128481,
abstract = {{2H,3′H-Spiro[benzofuran-3,2′-naphthoquinones], constituting a new spiroheterocyclic skeleton, were synthesized starting from 2-aryloxymethyl-1,4-naphthoquinones by means of a palladium(II)-catalyzed reaction, which is a new spirocyclic transformation. Under optimal conditions, i.e. 10 mol % of palladium(II) acetate, 15 mol % of 3,5-dichloropyridine, and 5 mol % of trifluoroacetic acid in acetic acid at 110 °C, various 2H,3′H-spiro[benzofuran-3,2′-naphthoquinones] were synthesized in yields strongly dependent on the substitution pattern of the aryloxy group. Unsubstituted or ortho-substituted 2-aryloxymethyl-1,4-quinones were found to rearrange toward the corresponding 2-(4-hydroxyaryl)-1,4-quinones upon treatment with trifluoroacetic acid.}},
author = {{Claes, Pieter and Jacobs, Jan and Kesteleyn, Bart and Van, Tuyen Nguyen and De Kimpe, Norbert}},
issn = {{0022-3263}},
journal = {{JOURNAL OF ORGANIC CHEMISTRY}},
keywords = {{palladium(II)-catalysis,4-quinones,spiroquinones,2-Aryloxymethyl-1,ARYLATIONS,DERIVATIVES,CATALYST,QUINONES,2 NAPHTHOQUINONE ANTIBIOTICS}},
language = {{eng}},
number = {{17}},
pages = {{8330--8339}},
title = {{Palladium(II)-catalyzed synthesis of 2H,3'H‑spiro[benzofuran-3,2'-naphthoquinones]}},
url = {{http://doi.org/10.1021/jo400852z}},
volume = {{78}},
year = {{2013}},
}
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