Synthesis of Fullerotetrahydroquinolines via [4 + 2] Cycloaddition Reaction of [60]Fullerene with in Situ Generated Aza-o-quinone Methides

Sheng-Peng Jiang; Wen-Qiang Lu; Zhan Liu; Guan-Wu Wang

doi:10.1021/acs.joc.7b02897

Synthesis of Fullerotetrahydroquinolines via [4 + 2] Cycloaddition Reaction of [60]Fullerene with in Situ Generated Aza-o-quinone Methides

J Org Chem. 2018 Feb 16;83(4):1959-1968. doi: 10.1021/acs.joc.7b02897. Epub 2018 Feb 5.

Authors

Sheng-Peng Jiang¹, Wen-Qiang Lu¹, Zhan Liu¹, Guan-Wu Wang^{1

2}

Affiliations

¹ CAS Key Laboratory of Soft Matter Chemistry, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), 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.
² State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou, Gansu 730000, P. R. China.

PMID: 29359561
DOI: 10.1021/acs.joc.7b02897

Abstract

An efficient [4 + 2] cycloaddition reaction of [60]fullerene with the in situ generated aza-o-quinone methides from N-(o-chloromethyl)aryl sulfonamides with the assistance of Cu₂O has been developed to afford a series of fullerotetrahydroquinolines. This strategy exhibits a broad substrate scope and excellent functional group tolerance. A tentative reaction pathway for the formation of fullerotetrahydroquinolines is proposed on the basis of the experimental results.

Publication types

Research Support, Non-U.S. Gov't