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Yugandar S, Konda S, Ila H. Amine Directed Pd(II)-Catalyzed C-H Activation-Intramolecular Amination of N-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles. J Org Chem. 2016;81(5):2035-52doi: 10.1021/acs.joc.5b02902.
Yugandar, S., Konda, S., & Ila, H. (2016). Amine Directed Pd(II)-Catalyzed C-H Activation-Intramolecular Amination of N-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles. The Journal of organic chemistry, 81(5), 2035-52. https://doi.org/10.1021/acs.joc.5b02902
Yugandar, Somaraju, et al. "Amine Directed Pd(II)-Catalyzed C-H Activation-Intramolecular Amination of N-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles." The Journal of organic chemistry vol. 81,5 (2016): 2035-52. doi: https://doi.org/10.1021/acs.joc.5b02902
Yugandar S, Konda S, Ila H. Amine Directed Pd(II)-Catalyzed C-H Activation-Intramolecular Amination of N-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles. J Org Chem. 2016 Mar 04;81(5):2035-52. doi: 10.1021/acs.joc.5b02902. Epub 2016 Feb 18. PMID: 26842134.
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J Org Chem. 2016 Mar 04;81(5):2035-52. doi: 10.1021/acs.joc.5b02902. Epub 2016 Feb 18.

Amine Directed Pd(II)-Catalyzed C-H Activation-Intramolecular Amination of N-Het(aryl)/Acyl Enaminonitriles and Enaminones: An Approach towards Multisubstituted Indoles and Heterofused Pyrroles.

The Journal of organic chemistry

Somaraju Yugandar, Saidulu Konda, Hiriyakkanavar Ila

Affiliations

  1. New Chemistry Unit , Jawaharlal Nehru Centre for Advanced Scientific Research, Jakkur, Bangalore-560064, India.

PMID: 26842134 DOI: 10.1021/acs.joc.5b02902

Abstract

An efficient route to multisubstituted indoles has been developed through intramolecular oxidative C-H activation-amination of readily available 2-(het)aryl-3-(het)aryl/alkyl-3-(het)aryl/acylaminoacrylonitrile/enaminone precursors in the presence of either palladium acetate/cupric acetate catalytic system under oxygen atmosphere or palladium acetate/silver carbonate in the presence of pivalic acid as additive. The method is compatible with a diverse range of substituents on the aryl ring as well as at the 2- and 3-positions of the indole ring. The versatility of this method was further demonstrated by elaborating it for the synthesis of heterofused pyrroles such as thieno[2,3-b]pyrroles, thieno[3,2-b]pyrroles, pyrrolo[2,3-b]indoles, and pyrrolo[2,3-b]pyridines in good yields. Probable mechanisms for the formation of these indoles have been suggested.

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