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Palladium-catalyzed indolization of N-aroylbenzotriazoles with disubstituted alkynes.
Org Lett. 2009 Mar 05; 11(5):1055-8.OL

Abstract

The palladium-catalyzed denitrogenative indolization of N-aroylbenzotriazoles 1 and internal alkynes 2 produced the corresponding polysubstituted indoles 3 in good to high yields. For example, the reaction of 5,6-dimethyl-1-[4-(trifluoromethyl)benzoyl]benzotriazole (1j) with 6-dodecyne (2a), 4-octyne (2b), and diphenylacetylene (2f) in the presence of 10 mol % of Pd(PPh(3))(4) without solvent at 130 degrees C gave the corresponding indoles 3i, 3l, and 3p in 74, 71, and 41% yields, respectively. In the present reaction, the aroylbenzotriazole acts as a synthetic equivalent of a 2-haloanilide in Larock's indole synthesis.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Nakamura I
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. itaru-n@mail.tains.tohoku.ac.jp
Nemoto T
No affiliation info available
Shiraiwa N
No affiliation info available
Terada M
No affiliation info available

MeSH

AlkynesCatalysisIndolesMolecular StructurePalladiumTriazoles

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19243194

Citation

Nakamura, Itaru, et al. "Palladium-catalyzed Indolization of N-aroylbenzotriazoles With Disubstituted Alkynes." Organic Letters, vol. 11, no. 5, 2009, pp. 1055-8.
Nakamura I, Nemoto T, Shiraiwa N, et al. Palladium-catalyzed indolization of N-aroylbenzotriazoles with disubstituted alkynes. Org Lett. 2009;11(5):1055-8.
Nakamura, I., Nemoto, T., Shiraiwa, N., & Terada, M. (2009). Palladium-catalyzed indolization of N-aroylbenzotriazoles with disubstituted alkynes. Organic Letters, 11(5), 1055-8. https://doi.org/10.1021/ol900113f
Nakamura I, et al. Palladium-catalyzed Indolization of N-aroylbenzotriazoles With Disubstituted Alkynes. Org Lett. 2009 Mar 5;11(5):1055-8. PubMed PMID: 19243194.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed indolization of N-aroylbenzotriazoles with disubstituted alkynes. AU - Nakamura,Itaru, AU - Nemoto,Tetsuya, AU - Shiraiwa,Naozumi, AU - Terada,Masahiro, PY - 2009/2/27/entrez PY - 2009/2/27/pubmed PY - 2010/8/25/medline SP - 1055 EP - 8 JF - Organic letters JO - Org Lett VL - 11 IS - 5 N2 - The palladium-catalyzed denitrogenative indolization of N-aroylbenzotriazoles 1 and internal alkynes 2 produced the corresponding polysubstituted indoles 3 in good to high yields. For example, the reaction of 5,6-dimethyl-1-[4-(trifluoromethyl)benzoyl]benzotriazole (1j) with 6-dodecyne (2a), 4-octyne (2b), and diphenylacetylene (2f) in the presence of 10 mol % of Pd(PPh(3))(4) without solvent at 130 degrees C gave the corresponding indoles 3i, 3l, and 3p in 74, 71, and 41% yields, respectively. In the present reaction, the aroylbenzotriazole acts as a synthetic equivalent of a 2-haloanilide in Larock's indole synthesis. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19243194/Palladium_catalyzed_indolization_of_N_aroylbenzotriazoles_with_disubstituted_alkynes_ L2 - https://doi.org/10.1021/ol900113f DB - PRIME DP - Unbound Medicine ER -