4.7 Article

Reaction of C60 with Inactive Secondary Amines and Aldehydes and the Cu(OAc)2-Promoted Regioselective Intramolecular C-H Functionalization of the Generated Fulleropyrrolidines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 22, Pages 11201-11209

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02193

Keywords

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Funding

  1. National Natural Science Foundation of China [21202011, 21272236]
  2. Natural Science Foundation of Jiangsu Province [BK20141171]
  3. Advanced Catalysis and Green Manufacturing Collaborative Innovation Center
  4. Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology [BM2012110]

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The thermal reaction of C-60 with aromatic aldehydes and inactive secondary amines for the stereoselective synthesis of trans-1,2,5-trisubstituted fulleropyrrolidines has been developed. Moreover, when an o-hydroxyl group was located at the phenyl ring of the generated fulleropyrrolidines, the Cu(OAc)(2)-promoted regioselective intramolecular C-O coupling reaction occurred to generate unique tricycle-fused fullerene derivatives.

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