Iodine-Catalyzed Oxidative Cross-Dehydrogenative Coupling of Quinoxalinones and Indoles: Synthesis of 3-(Indol-2-yl)quinoxalin-2-one under Mild and Ambient Conditions

Medena Noikham; Tanakorn Kittikool; Sirilata Yotphan

doi:10.1055/s-0037-1609445

Synthesis, Table of Contents

Synthesis 2018; 50(12): 2337-2346
DOI: 10.1055/s-0037-1609445

paper

Iodine-Catalyzed Oxidative Cross-Dehydrogenative Coupling of Quinoxalinones and Indoles: Synthesis of 3-(Indol-2-yl)quinoxalin-2-one under Mild and Ambient Conditions

Medena Noikham

Center of Excellence for Innovation in Chemistry (PERCH-CIC), Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand Email: sirilata.yot@mahidol.ac.th

,

Tanakorn Kittikool

Center of Excellence for Innovation in Chemistry (PERCH-CIC), Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand Email: sirilata.yot@mahidol.ac.th

,

Sirilata Yotphan *

Center of Excellence for Innovation in Chemistry (PERCH-CIC), Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand Email: sirilata.yot@mahidol.ac.th

› Author Affiliations

Abstract

All articles of this category

Abstract

A highly efficient iodine-catalyzed oxidative cross-dehydrogenative coupling reaction of quinoxalinones and indoles has been developed. Without the requirement of peroxide and acid, this reaction utilizes a catalytic amount of molecular iodine to facilitate the C–C bond formation under ambient air. This simple and easy-to-handle protocol represents an interesting synthetic alternative with a good scope and functional group compatibility.

Key words

iodine - quinoxalinone - indole - oxidative coupling - metal-free

Full Text

References

References

For selected reviews, see:

1a Li C.-J. Acc. Chem. Res. 2009; 42: 335
1b Yeung CS. Dong VM. Chem. Rev. 2011; 111: 1215
1c Waterman R. Chem. Soc. Rev. 2013; 42: 5629
1d Li C.-J. From C–H to C–C Bonds: Cross-Dehydrogenative-Coupling . Royal Society of Chemistry; Cambridge: 2014
1e Kozlowski MC. Acc. Chem. Res. 2017; 50: 638
1f Qin Y. Zhu L. Luo S. Chem. Rev. 2017; 117: 9433
1g Lakshman MK. Vuram PK. Chem. Sci. 2017; 8: 5845

For selected reviews and recent examples, see:

2a Ashenhurst JA. Chem. Soc. Rev. 2010; 39: 540
2b Le Bras J. Muzart J. Chem. Rev. 2011; 111: 1170
2c Shi Z. Zhang C. Tang C. Jiao N. Chem. Soc. Rev. 2012; 41: 3381
2d Song G. Wang F. Li X. Chem. Soc. Rev. 2012; 41: 3651
2e Mousseau JJ. Charette AB. Acc. Chem. Res. 2013; 46: 412
2f Li B. Dixneuf PH. Chem. Soc. Rev. 2013; 42: 5744
2g Girard SA. Knauber T. Li CJ. Angew. Chem. Int. Ed. 2014; 53: 74
2h Yang Y. Lan J. You J. Chem. Rev. 2017; 117: 8787
2i Pan C. Huang B. Hu W. Feng X. Yu J.-T. J. Org. Chem. 2016; 81: 2087
2j Sharma R. Abdullaha M. Bharate SB. J. Org. Chem. 2017; 82: 9786
2k Chen X. Cui X. Yang F. Wu Y. Org. Lett. 2015; 17: 1445
2l Varun BV. Dhineshkumar J. Bettadapur KR. Siddaraju Y. Alagiri K. Prabhu KR. Tetrahedron Lett. 2017; 58: 803

3 Liu C. Yuan J. Gao M. Tang S. Li W. Shi R. Lei A. Chem. Rev. 2015; 115: 12138