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Issue 4, 2017
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Regioselective acylation and carboxylation of [60]fulleroindoline via electrochemical synthesis

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Abstract

A regioselective and highly efficient electrochemical method for direct acylation and carboxylation of a [60]fulleroindoline has been developed. By using inexpensive and readily available acyl chlorides and chloroformates, both keto and ester groups can be easily attached onto the fullerene skeleton to afford 1,2,3,16-functionalized [60]fullerene derivatives regioselectively. In addition, a plausible mechanism for the formation of fullerenyl ketones and esters is proposed, and their further transformations under basic and acidic conditions have been investigated.

Graphical abstract: Regioselective acylation and carboxylation of [60]fulleroindoline via electrochemical synthesis

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Publication details

The article was received on 23 Oct 2016, accepted on 20 Jan 2017 and first published on 23 Jan 2017


Article type: Research Article
DOI: 10.1039/C6QO00654J
Citation: Org. Chem. Front., 2017,4, 603-607
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    Regioselective acylation and carboxylation of [60]fulleroindoline via electrochemical synthesis

    H. Lin, Y. Matsuo, J. Wang and G. Wang, Org. Chem. Front., 2017, 4, 603
    DOI: 10.1039/C6QO00654J

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