Issue 12, 2011
From the journal:

Green Chemistry

Graphene oxide and Rose Bengal: oxidative C–H functionalisation of tertiary amines using visible light†

Yuanhang Pan,a   Shuai Wang,c   Choon Wee Kee,a   Emilie Dubuisson,a   Yuanyong Yang,a   Kian Ping Loha  and  Choon-Hong Tan*ab  

* Corresponding authors

a Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore
E-mail: chmtanch@nus.edu.sg
Fax: (+65) 6779 1691
Tel: (+65) 6516 2845

b Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan, P.R. China

c School of Chemistry & Chemical Engineering, Huazhong University of Science and Technology, Wuhan, Hebei, P.R. China

Abstract

Visible light induced oxidative C–H functionalisation of tertiary amines catalysed by the combination of graphene oxide and Rose Bengal was developed. This reaction avoids the use of stoichiometric amounts of peroxy compounds as terminal oxidants. This reaction is useful for tri-alkyl amines including chiral tertiary amines. Both cyanide and trifluoromethyl nucleophiles were shown to participate in this reaction, providing α-cyano- and α-trifluoromethylated tertiary amines.

Graphical abstract: Graphene oxide and Rose Bengal: oxidative C–H functionalisation of tertiary amines using visible light

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Article information

DOI
https://doi.org/10.1039/C1GC15865A
Article type
Communication
Submitted
18 Jul 2011
Accepted
20 Sep 2011
First published
13 Oct 2011

Green Chem., 2011,13, 3341-3344

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Graphene oxide and Rose Bengal: oxidative C–H functionalisation of tertiary amines using visible light

Y. Pan, S. Wang, C. W. Kee, E. Dubuisson, Y. Yang, K. P. Loh and C. Tan, Green Chem., 2011, 13, 3341 DOI: 10.1039/C1GC15865A

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