Cu(II)-catalyzed highly regio- and stereoselective construction of C–C double bonds: an efficient method for the ketonization–olefination of indoles

Yun-Hong Bao; Jia-Yi Zhu; Wen-Bing Qin; Yu-Bo Kong; Zheng-Wang Chen; Shao-Bin Tang; Liang-Xian Liu

doi:10.1039/C3OB41589A

Cu(II)-catalyzed highly regio- and stereoselective construction of C–C double bonds: an efficient method for the ketonization–olefination of indoles

Yun-Hong Bao,^a Jia-Yi Zhu,^a Wen-Bing Qin,^a Yu-Bo Kong,^a Zheng-Wang Chen,^a Shao-Bin Tang^a and Liang-Xian Liu*^a

* Corresponding authors

^a Department of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou, P. R. China
E-mail: lxliu@xmu.edu.cn

Abstract

A general and efficient method for the cross-coupling of indoles with β-keto esters by using TEMPO/CuSO₄·5H₂O in air as oxidant has been developed. This reaction features high functional-group compatibility and an excellent selectivity. This methodology provides an alternative approach for the ketonization–olefination of indoles in moderate to good yields.

Supplementary files

Publication details

The article was received on 03 Aug 2013, accepted on 19 Sep 2013 and first published on 19 Sep 2013

Article type: Paper

DOI: 10.1039/C3OB41589A

Citation: Org. Biomol. Chem., 2013,11, 7938-7945

Request permissions
Cu(II)-catalyzed highly regio- and stereoselective construction of C–C double bonds: an efficient method for the ketonization–olefination of indoles

Y. Bao, J. Zhu, W. Qin, Y. Kong, Z. Chen, S. Tang and L. Liu, Org. Biomol. Chem., 2013, 11, 7938
DOI: 10.1039/C3OB41589A
If you are not the author of this article and you wish to reproduce material from it in a third party non-RSC publication you must formally request permission using RightsLink. Go to our Instructions for using RightsLink page for details.

Authors contributing to RSC publications (journal articles, books or book chapters) do not need to formally request permission to reproduce material contained in this article provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:
For reproduction of material from NJC:
Reproduced from Ref. XX with permission from the Centre National de la Recherche Scientifique (CNRS) and The Royal Society of Chemistry.

For reproduction of material from PCCP:
Reproduced from Ref. XX with permission from the PCCP Owner Societies.

For reproduction of material from PPS:
Reproduced from Ref. XX with permission from the European Society for Photobiology, the European Photochemistry Association, and The Royal Society of Chemistry.

For reproduction of material from all other RSC journals and books:
Reproduced from Ref. XX with permission from The Royal Society of Chemistry.
If the material has been adapted instead of reproduced from the original RSC publication "Reproduced from" can be substituted with "Adapted from".

In all cases the Ref. XX is the XXth reference in the list of references.

If you are the author of this article you do not need to formally request permission to reproduce figures, diagrams etc. contained in this article in third party publications or in a thesis or dissertation provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:
For reproduction of material from NJC:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC

For reproduction of material from PCCP:
[Original citation] - Reproduced by permission of the PCCP Owner Societies

For reproduction of material from PPS:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC

For reproduction of material from all other RSC journals:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry
If you are the author of this article you still need to obtain permission to reproduce the whole article in a third party publication with the exception of reproduction of the whole article in a thesis or dissertation.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Organic & Biomolecular Chemistry

Cu(II)-catalyzed highly regio- and stereoselective construction of C–C double bonds: an efficient method for the ketonization–olefination of indoles

Abstract

Supplementary files

Publication details

Cu(II)-catalyzed highly regio- and stereoselective construction of C–C double bonds: an efficient method for the ketonization–olefination of indoles

Search articles by author

Spotlight

Advertisements