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Issue 4, 2017
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Convenient synthesis of 6-alkyl phenanthridines and 1-alkyl isoquinolines via silver-catalyzed oxidative radical decarboxylation

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Abstract

A convenient and efficient protocol for the synthesis of 6-alkyl phenanthridines and 1-alkyl isoquinolines has been developed. The reaction relies on the coupling of 2-isocyanobiphenyls and vinyl isonitriles with alkyl radicals formed by the silver-catalyzed decarboxylation of stoichiometric aliphatic carboxylic acids, and affords diverse phenanthridine and isoquinoline derivatives under mild reaction conditions. The experiment of β-scission of cyclobutylcarbinyl radicals is used to shed light on the reaction mechanism.

Graphical abstract: Convenient synthesis of 6-alkyl phenanthridines and 1-alkyl isoquinolines via silver-catalyzed oxidative radical decarboxylation

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Publication details

The article was received on 26 Oct 2016, accepted on 23 Dec 2016 and first published on 23 Dec 2016


Article type: Paper
DOI: 10.1039/C6OB02331B
Citation: Org. Biomol. Chem., 2017,15, 957-971

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    Convenient synthesis of 6-alkyl phenanthridines and 1-alkyl isoquinolines via silver-catalyzed oxidative radical decarboxylation

    Q. Yao, X. Zhou, X. Zhang, C. Wang, P. Wang and M. Li, Org. Biomol. Chem., 2017, 15, 957
    DOI: 10.1039/C6OB02331B

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