Copper-Catalyzed S-Arylation of Arylthioureas by Using Diaryl­iodonium Salts

Hui Zhu; Xing Liu; Yu Cheng; Han-Ying Peng; Yue-Sheng Li; Zhi-Bing Dong

doi:10.1055/s-0036-1591569

Synthesis, Table of Contents

Synthesis 2018; 50(11): 2247-2254
DOI: 10.1055/s-0036-1591569

paper

Copper-Catalyzed S-Arylation of Arylthioureas by Using Diaryliodonium Salts

Hui Zhu

^aSchool of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China Email: dzb04982@wit.edu.cn

,

Xing Liu

^aSchool of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China Email: dzb04982@wit.edu.cn

,

Yu Cheng

^aSchool of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China Email: dzb04982@wit.edu.cn

,

Han-Ying Peng

^aSchool of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China Email: dzb04982@wit.edu.cn

,

Yue-Sheng Li*

^bNonpower Nuclear Technology Collaborative Innovation Center, Hubei University of Science & Technology, Xianning 437100, P. R. of China Email: frank78929@163.com

,

Zhi-Bing Dong*

^aSchool of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China Email: dzb04982@wit.edu.cn

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Abstract

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Abstract

A convenient and efficient copper-catalyzed S-arylation of arylthioureas using diaryliodonium salts is reported. The desired arylisothioureas were synthesized in good yields in the presence of CuCl as catalyst and K₂CO₃ as base, and a wide variety of functional groups on the arylthioureas and diaryliodonium salts were tolerated. The protocol affords an alternative synthesis of some potentially useful biological and pharmaceutical compounds.

Key words

copper - S-arylation - arylthioureas - diaryliodonium salts - synthesis

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References

References

1a Bean GJ. Flickinger ST. Westler WM. McCully ME. Sept D. Weibel DB. Amann KJ. Biochemistry 2009; 48: 4852
1b Paesano N. Marzocco S. Vicidomini C. Saturnino C. Autore G. Sbardella G. Bioorg. Med. Chem. Lett. 2005; 15: 539
1c Rogovoy B. Vvedenskiy V. Cai X. Chassaing C. Katritzky AR. Forood B. (Lion Bioscience AG). WO 2003095396, 2003
1d Gross M. Held P. Vogel R. (VEB Fahlberg-List, Chemische und Pharmazeutische Fabriken). DE 2035907, 1971
1e Zhang J. McCarthy TJ. Moore WM. Currie MG. Welch MJ. J. Med. Chem. 1996; 39: 5110

2 Katritzky AR. Cai XH. Vvedensky VY. Rogovoy BV. Forood B. Hebert N. Heterocycles 2002; 57: 1799
3 Dang Q. Brown BS. Liu Y. Rydzewski RM. Robinson ED. Poelje PD. Reddy MR. Eroin MD. J. Med. Chem. 2009; 52: 2880
4 Khalili G. Monatsh. Chem. 2015; 146: 1891

5a Biswas K. Greaney MF. Org. Lett. 2011; 13: 4946
5b Ley K. Eholzer DU. Angew. Chem. 1966; 78: 672
5c Dawra N. Ram RN. Synthesis 2016; 48: 4199
5d Yavari I. Nematpour M. Damghani T. Tetrahedron Lett. 2014; 55: 1323

6a Martin FM. Synthesis 2017; 49: 1905
6b Yang MN. Yan DM. Zhao QQ. Chen JR. Xiao WJ. Org. Lett. 2017; 19: 5208
6c Duan YN. Jiang S. Han YC. Sun B. Zhang C. Chin. J. Org. Chem. 2016; 36: 1973
6d Christopher JT. Shariar MA. S. Danielle LB. Sachin GM. Michael FG. Angew. Chem. Int. Ed. 2017; 56: 5263

7a Zhdankin VV. Stang PJ. Chem. Rev. 2008; 108: 5299
7b Silva LF. Olofsson B. Nat. Prod. Rep. 2011; 28: 1722
7c Merritt EA. Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052
7d Yoshimura A. Zhdankin VV. Chem. Rev. 2016; 116: 3328

8 Zhu H. Liu X. Chang C.-Z. Dong Z.-B. Synthesis 2017; 49: 5211

9a Xu W. Zeng M.-T. Liu M. Liu S.-S. Li Y.-S. Dong Z.-B. Synthesis 2017; 49: 3084
9b Xu W. Zeng M.-T. Liu M. Liu X. Chang C.-Z. Zhu H. Li Y.-S. Dong Z.-B. Chem. Lett. 2017; 46: 641
9c Dong Z.-B. Wang M. Zhu H. Liu X. Chang C.-Z. Synthesis 2017; 49: 5258
9d Liu M. Zeng M.-T. Xu W. Wu L. Dong Z.-B. Tetrahedron Lett. 2017; 58: 4352
9e Xu W. Zeng M.-T. Liu S.-S. Li Y.-S. Dong Z.-B. Tetrahedron Lett. 2017; 58: 4289
9f Liu X. Liu M. Xu W. Zeng M.-T. Zhu H. Chang C.-Z. Dong Z.-B. Green Chem. 2017; 19: 5591
9g Dong Z.-B. Liu X. Bolm C. Org. Lett. 2017; 19: 5916
9h Zeng M.-T. Xu W. Liu X. Chang C.-Z. Zhu H. Dong Z.-B. Eur. J. Org. Chem. 2017; 6060
9i Liu X. Cao Q. Xu W. Zeng M.-T. Dong Z.-B. Eur. J. Org. Chem. 2017; 5795
9j Zeng M.-T. Wang M. Peng H.-Y. Cheng Y. Dong Z.-B. Synthesis 2018; 50: 644
9k Cheng Y. Liu X. Dong Z.-B. Eur. J. Org. Chem. 2018; 815
9l Xu W. Gao F. Dong Z.-B. Eur. J. Org. Chem. 2018; 821
9m Cao Q. Peng H.-Y. Cheng Y. Dong Z.-B. Synthesis 2018; 50: 1527

10a Hickman AJ. Sanford MS. Nature 2012; 484: 177
10b Casitas A. Ribas X. Chem. Sci. 2013; 4: 2301
10c Bhong BY. Shelke AV. Karade NN. Tetrahedron Lett. 2013; 54: 739
10d Lee OS. Lee HK. Kim H. Shin H. Sohn J.-H. Tetrahedron 2015; 71: 2936

Supplementary Material

Supporting Information

Copper-Catalyzed S-Arylation of Arylthioureas by Using Diaryl­iodonium Salts

Copper-Catalyzed S-Arylation of Arylthioureas by Using Diaryliodonium Salts