Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Copper-Promoted Synthesis of 2-Fulleropyrrolines via Heteroannulation of [60]Fullerene with α-Amino Ketones

Copper-Promoted Synthesis of 2-Fulleropyrrolines via Heteroannulation of [60]Fullerene with α-Amino Ketones
Qing-Hua Wu, Sheng-Peng Jiang, Guan-Wu Wang
A Cu(OAc)2-promoted heteroannulation of [60]fullerene with α-amino ketones has been exploited for the efficient synthesis of 2-fulleropyrrolines containing a trisubstituted or tetrasubstituted C═C bond via the formation of C–C and C–N bonds. Mechanistic study indicates that a radical process should be involved in this transformation. Furthermore, theoretical computations show that the process via the attack of the carbon radical generated from the employed α-amino ketone to [60]fullerene should be the preferred pathway. The electrochemical properties of the synthesized 2-fulleropyrrolines have also been investigated.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01237

DOI: 10.1021/acs.joc.7b01237

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