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Rhodium-catalyzed intramolecular hydroarylation of 1-halo-1-alkynes: regioselective synthesis of semihydrogenated aromatic heterocycles.
Chemistry. 2014 Jan 03; 20(1):317-22.C

Abstract

The regioselective intramolecular hydroarylation of (3-halo-2-propynyl)anilines, (3-halo-2-propynyl) aryl ethers, or (4-halo-3-butynyl) aryl ethers was efficiently catalyzed by Rh2(OCOCF3)4 to give semihydrogenated aromatic heterocycles, such as 4-halo-1,2-dihydroquinolines, 4-halo-3-chromenes, or 4-(halomethylene)chromans, in good to excellent yields. Some synthetic applications taking advantage of the halo-substituents of the products are also illustrated.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Murase H
Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-59 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501 (Japan), Fax: (+81) (0)45-924-5849.
Senda K
No affiliation info available
Senoo M
No affiliation info available
Hata T
No affiliation info available
Urabe H
No affiliation info available

MeSH

AlkynesBenzopyransCatalysisCoordination ComplexesHeterocyclic CompoundsHydrogenationQuinolinesRhodiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

24302566

Citation

Murase, Hirohiko, et al. "Rhodium-catalyzed Intramolecular Hydroarylation of 1-halo-1-alkynes: Regioselective Synthesis of Semihydrogenated Aromatic Heterocycles." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 20, no. 1, 2014, pp. 317-22.
Murase H, Senda K, Senoo M, et al. Rhodium-catalyzed intramolecular hydroarylation of 1-halo-1-alkynes: regioselective synthesis of semihydrogenated aromatic heterocycles. Chemistry. 2014;20(1):317-22.
Murase, H., Senda, K., Senoo, M., Hata, T., & Urabe, H. (2014). Rhodium-catalyzed intramolecular hydroarylation of 1-halo-1-alkynes: regioselective synthesis of semihydrogenated aromatic heterocycles. Chemistry (Weinheim an Der Bergstrasse, Germany), 20(1), 317-22. https://doi.org/10.1002/chem.201303008
Murase H, et al. Rhodium-catalyzed Intramolecular Hydroarylation of 1-halo-1-alkynes: Regioselective Synthesis of Semihydrogenated Aromatic Heterocycles. Chemistry. 2014 Jan 3;20(1):317-22. PubMed PMID: 24302566.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed intramolecular hydroarylation of 1-halo-1-alkynes: regioselective synthesis of semihydrogenated aromatic heterocycles. AU - Murase,Hirohiko, AU - Senda,Kousuke, AU - Senoo,Masato, AU - Hata,Takeshi, AU - Urabe,Hirokazu, Y1 - 2013/12/02/ PY - 2013/07/31/received PY - 2013/12/5/entrez PY - 2013/12/5/pubmed PY - 2014/8/26/medline KW - chromene KW - dihydroquinolines KW - heterocycles KW - hydroarylation KW - rhodium SP - 317 EP - 22 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 20 IS - 1 N2 - The regioselective intramolecular hydroarylation of (3-halo-2-propynyl)anilines, (3-halo-2-propynyl) aryl ethers, or (4-halo-3-butynyl) aryl ethers was efficiently catalyzed by Rh2(OCOCF3)4 to give semihydrogenated aromatic heterocycles, such as 4-halo-1,2-dihydroquinolines, 4-halo-3-chromenes, or 4-(halomethylene)chromans, in good to excellent yields. Some synthetic applications taking advantage of the halo-substituents of the products are also illustrated. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/24302566/Rhodium_catalyzed_intramolecular_hydroarylation_of_1_halo_1_alkynes:_regioselective_synthesis_of_semihydrogenated_aromatic_heterocycles_ DB - PRIME DP - Unbound Medicine ER -