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Synthesis of functionalized 1H-indenes via copper-catalyzed arylative cyclization of arylalkynes with aromatic sulfonyl chlorides.
J Am Chem Soc. 2011 Nov 09; 133(44):17638-40.JA

Abstract

A variety of polysubstituted 1H-indenes can be prepared through the copper-catalyzed arylative cyclization of simple arylalkynes with commercially available aromatic sulfonyl chlorides that function as an aryl group donor. The reaction tolerates a broad range of functional groups, including bromide and iodide, nitrile, ketone, and nitro groups. The reaction allowed the synthesis of polycyclic aromatic hydrocarbons, such as a bis(indene), indacene, and fused polyarene derivatives, some of them showing strong fluorescence in solution and the solid state.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zeng X
Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Ilies L
No affiliation info available
Nakamura E
No affiliation info available

MeSH

AlkynesCatalysisCopperCyclizationIndenesMolecular StructureStereoisomerismSulfinic Acids

Pub Type(s)

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

Language

eng

PubMed ID

21988538

Citation

Zeng, Xiaoming, et al. "Synthesis of Functionalized 1H-indenes Via Copper-catalyzed Arylative Cyclization of Arylalkynes With Aromatic Sulfonyl Chlorides." Journal of the American Chemical Society, vol. 133, no. 44, 2011, pp. 17638-40.
Zeng X, Ilies L, Nakamura E. Synthesis of functionalized 1H-indenes via copper-catalyzed arylative cyclization of arylalkynes with aromatic sulfonyl chlorides. J Am Chem Soc. 2011;133(44):17638-40.
Zeng, X., Ilies, L., & Nakamura, E. (2011). Synthesis of functionalized 1H-indenes via copper-catalyzed arylative cyclization of arylalkynes with aromatic sulfonyl chlorides. Journal of the American Chemical Society, 133(44), 17638-40. https://doi.org/10.1021/ja209300c
Zeng X, Ilies L, Nakamura E. Synthesis of Functionalized 1H-indenes Via Copper-catalyzed Arylative Cyclization of Arylalkynes With Aromatic Sulfonyl Chlorides. J Am Chem Soc. 2011 Nov 9;133(44):17638-40. PubMed PMID: 21988538.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of functionalized 1H-indenes via copper-catalyzed arylative cyclization of arylalkynes with aromatic sulfonyl chlorides. AU - Zeng,Xiaoming, AU - Ilies,Laurean, AU - Nakamura,Eiichi, Y1 - 2011/10/17/ PY - 2011/10/13/entrez PY - 2011/10/13/pubmed PY - 2012/3/1/medline SP - 17638 EP - 40 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 133 IS - 44 N2 - A variety of polysubstituted 1H-indenes can be prepared through the copper-catalyzed arylative cyclization of simple arylalkynes with commercially available aromatic sulfonyl chlorides that function as an aryl group donor. The reaction tolerates a broad range of functional groups, including bromide and iodide, nitrile, ketone, and nitro groups. The reaction allowed the synthesis of polycyclic aromatic hydrocarbons, such as a bis(indene), indacene, and fused polyarene derivatives, some of them showing strong fluorescence in solution and the solid state. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/21988538/Synthesis_of_functionalized_1H_indenes_via_copper_catalyzed_arylative_cyclization_of_arylalkynes_with_aromatic_sulfonyl_chlorides_ L2 - https://doi.org/10.1021/ja209300c DB - PRIME DP - Unbound Medicine ER -