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Palladium(0)-catalyzed single and double isonitrile insertion: a facile synthesis of benzofurans, indoles, and isatins.
Chemistry. 2015 Jan 12; 21(3):998-1003.C

Abstract

A palladium(0)-catalyzed cascade process consisting of isonitrile insertion and α-Csp(3)-H cross-coupling can be achieved for the synthesis of benzofurans and indoles. The construction of isatins by a Pd-catalyzed cascade reaction incorporating double isonitrile insertion, amination, and hydrolysis has also been achieved. The key features of this work include diverse heterocycle synthesis, phosphine-ligand-free reaction conditions, a one-pot procedure, simple and commercially available starting materials, broad functional-group compatibility, and moderate to good reaction yields.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Senadi GC
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, No. 100, Shih-Chuan 1 st Rd, Sanmin district, Kaohsiung City, 807 (Taiwan).
Hu WP
No affiliation info available
Boominathan SS
No affiliation info available
Wang JJ
No affiliation info available

MeSH

AminationBenzofuransCatalysisHydrolysisIndolesIsatinNitrilesPalladium

Pub Type(s)

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

Language

eng

PubMed ID

25447489

Citation

Senadi, Gopal Chandru, et al. "Palladium(0)-catalyzed Single and Double Isonitrile Insertion: a Facile Synthesis of Benzofurans, Indoles, and Isatins." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 21, no. 3, 2015, pp. 998-1003.
Senadi GC, Hu WP, Boominathan SS, et al. Palladium(0)-catalyzed single and double isonitrile insertion: a facile synthesis of benzofurans, indoles, and isatins. Chemistry. 2015;21(3):998-1003.
Senadi, G. C., Hu, W. P., Boominathan, S. S., & Wang, J. J. (2015). Palladium(0)-catalyzed single and double isonitrile insertion: a facile synthesis of benzofurans, indoles, and isatins. Chemistry (Weinheim an Der Bergstrasse, Germany), 21(3), 998-1003. https://doi.org/10.1002/chem.201405933
Senadi GC, et al. Palladium(0)-catalyzed Single and Double Isonitrile Insertion: a Facile Synthesis of Benzofurans, Indoles, and Isatins. Chemistry. 2015 Jan 12;21(3):998-1003. PubMed PMID: 25447489.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium(0)-catalyzed single and double isonitrile insertion: a facile synthesis of benzofurans, indoles, and isatins. AU - Senadi,Gopal Chandru, AU - Hu,Wan-Ping, AU - Boominathan,Siva Senthil Kumar, AU - Wang,Jeh-Jeng, Y1 - 2014/11/28/ PY - 2014/11/03/received PY - 2014/12/3/entrez PY - 2014/12/3/pubmed PY - 2015/9/12/medline KW - benzofurans KW - indoles KW - insertion KW - isatins KW - palladium SP - 998 EP - 1003 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 21 IS - 3 N2 - A palladium(0)-catalyzed cascade process consisting of isonitrile insertion and α-Csp(3)-H cross-coupling can be achieved for the synthesis of benzofurans and indoles. The construction of isatins by a Pd-catalyzed cascade reaction incorporating double isonitrile insertion, amination, and hydrolysis has also been achieved. The key features of this work include diverse heterocycle synthesis, phosphine-ligand-free reaction conditions, a one-pot procedure, simple and commercially available starting materials, broad functional-group compatibility, and moderate to good reaction yields. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/25447489/Palladium_0__catalyzed_single_and_double_isonitrile_insertion:_a_facile_synthesis_of_benzofurans_indoles_and_isatins_ DB - PRIME DP - Unbound Medicine ER -