CAS Key Laboratory of Soft Matter Chemistry, Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), Hefei National Laboratory for Physical Sciences at Microscale, and Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, P.R. China.
State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou, Gansu 730000, P.R. China.
J Org Chem. 2017 Oct 20;82(20):10823-10829. doi: 10.1021/acs.joc.7b01237. Epub 2017 Sep 29.
A Cu(OAc)-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.
Cu(OAc)促进的[60]富勒烯与α-氨基酮的杂环化反应，通过形成 C-C 和 C-N 键，高效合成了含有三取代或四取代 C=C 键的 2-富勒吡咯啉。机理研究表明，该转化过程中应涉及自由基过程。此外，理论计算表明，通过所使用的α-氨基酮生成的碳自由基进攻[60]富勒烯的过程应该是首选途径。所合成的 2-富勒吡咯啉的电化学性质也进行了研究。
