Synthesis 2018; 50(07): 1527-1534
DOI: 10.1055/s-0036-1589166
paper
© Georg Thieme Verlag Stuttgart · New York

A Highly Efficient CuCl2-Catalyzed C–S Coupling of Aryl Iodides with Tetraalkylthiuram Disulfides: Synthesis of Aryl Dithiocarbamates

Qiang Cao
School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China   Email: dzb04982@wit.edu.cn
,
Han-Ying Peng
School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China   Email: dzb04982@wit.edu.cn
,
Yu Cheng
School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China   Email: dzb04982@wit.edu.cn
,
Zhi-Bing Dong*
School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China   Email: dzb04982@wit.edu.cn
› Author Affiliations
National Natural Science Foundation of China (21302150), Hubei Provincial Department of Education (D20131501), Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry [2012]1707, foundation of Chutian distinguished fellow from Hubei Provincial Department of Education, foundation of High-end Talent Cultivation Program from Wuhan Institute of Technology. Z.-B. D. acknowledges the Humboldt Foundation and China Scholarship Council for a fellowship.
Further Information

Publication History

Received: 21 November 2017

Accepted after revision: 10 December 2017

Publication Date:
11 January 2018 (online)


These authors contributed equally to this work

Abstract

A highly efficient copper(II)-catalyzed C–S cross-coupling reaction of aryl iodides with tetraalkylthiuram disulfides was developed. With only 1 mol% of CuCl2 as catalyst, zinc powder as reductant, and K2CO3 as base, aryl iodides reacted with tetraalkylthiuram disulfides in DMSO furnishing the corresponding aryl dithiocarbamates in good to excellent yields. This protocol is an improvement of previous work, it features convenient performance, low addition of catalyst, no requirement for any ligand, and provides good yields. The method has a broad substrate scope and uses cheap and readily available starting materials.

Supporting Information

 
  • References

    • 1a Boas U. Gertz H. Christensen JB. Heegaard PM. H. Tetrahedron Lett. 2004; 45: 269
    • 1b Betou M. Male L. Steed JW. Grainger RS. Chem.–Eur. J. 2014; 20: 6505
  • 2 Kapanda CN. Masquelier J. Labar G. Muccioli GG. Poupaert JH. Lambert DM. J. Med. Chem. 2012; 55: 5774
  • 3 Bessho R. Matsubara K. Kubota M. Kuwakado K. Hirota H. Wakazono Y. Lin YW. Okuda A. Kawai M. Nishikomori R. Heike T. Biochem. Pharmacol. 1994; 48: 1883
  • 4 Wolfe JT. Ross D. Cohen GM. FEBS Lett. 1994; 352: 58
    • 5a Ronconi L. Marzano C. Zanello P. Corsini M. Miolo G. Macca C. Trevisan A. Fregona D. J. Med. Chem. 2006; 49: 1648
    • 5b Hou XL. Ge ZM. Wang TM. Guo W. Cui JR. Cheng TM. Lai CS. Li RT. Bioorg. Med. Chem. Lett. 2006; 16: 4214
    • 6a Urlyapova NG. Yushchenko AA. Daudova AD. Makarov VA. Bull. Exp. Biol. Med. 2007; 143: 327
    • 6b Nagano R. Shibata K. Naito T. Fuse A. Asano K. Hashizume T. Nakagawa S. Antimicrob. Agents Chemother. 1997; 41: 2278
    • 7a Li GY. Angew. Chem. Int. Ed. 2001; 40: 1513
    • 7b Murata M. Buchwald SL. Tetrahedron 2004; 60: 7397
    • 7c Fernandez-Rodriguez MA. Shen Q. Hartwig JF. Chem.–Eur. J. 2006; 12: 7782
    • 7d Fernández-Rodríguez MA. Shen Q. Hartwig JF. J. Am. Chem. Soc. 2006; 128: 2180
    • 8a Baldovino-Pantaleón O. Hernández-Ortega S. Morales-Morales D. Adv. Synth. Catal. 2006; 348: 236
    • 8b Jammi S. Barua P. Rout L. Saha P. Punniyamurthy T. Tetrahedron Lett. 2008; 49: 1484
    • 9a Sperotto E. van Klink GP. M. de Vries JG. van Koten G. J. Org. Chem. 2008; 73: 5625
    • 9b Xu HJ. Zhao YQ. Feng T. Feng YS. J. Org. Chem. 2012; 77: 2878
    • 10a Correa A. Carril M. Bolm C. Angew. Chem. Int. Ed. 2008; 47: 2880
    • 10b Wu JR. Lin CH. Lee CF. Chem. Commun. 2009; 4450
    • 10c Wu WY. Wang JC. Tsai FY. Green Chem. 2009; 11: 326
    • 11a Gronowitz S. Hornfeldt AB. Temciuc M. Synthesis 1993; 483
    • 11b Krasovskiy A. Gavryushin A. Knochel P. Synlett 2005; 2691
    • 11c Krasovskiy A. Malakhov V. Gavryushin A. Knochel P. Angew. Chem. Int. Ed. 2006; 45: 6040
    • 11d Krasovskiy A. Gavryushin A. Knochel P. Synlett 2006; 792
  • 12 Chen ZC. Jin YY. Stang PJ. J. Org. Chem. 1987; 52: 4117
  • 13 Closely related to the work reported here are Ullmann-type couplings of aryl iodides and vinyl bromides with sodium dithiocarbamates. However, this method requires more catalyst (CuI, 15 mol%) and ligand (N,N-dimethylglycine, 30 mol%). Furthermore, sodium dithiocarbamates are generally more expensive than the thiuram reagent used in the present work. See: Liu YY. Bao WL. Tetrahedron Lett. 2007; 48: 4785
  • 14 Azizi N. Aryanasab F. Saidi MR. Org. Lett. 2006; 8: 5275
  • 15 Bhadra S. Saha A. Ranu BC. Green Chem. 2008; 10: 1224
  • 16 Chatterjee T. Bhadra S. Ranu BC. Green Chem. 2011; 13: 1837
  • 17 Yin XG. Guo YM. Liu CB. Wang ZF. Zhang B. Tetrahedron Lett. 2015; 56: 5135
  • 18 Qi CR. Guo TZ. Xiong WF. Synlett 2016; 27: 2626
  • 19 Dong ZB. Liu X. Bolm C. Org. Lett. 2017; 19: 5916
    • 20a Xu W. Zeng MT. Liu M. Liu SS. Li YS. Dong ZB. Synthesis 2017; 49: 3084
    • 20b Xu W. Zeng MT. Liu M. Liu X. Chang CZ. Zhu H. Li YS. Dong ZB. Chem. Lett. 2017; 46: 641
    • 20c Zeng MT. Xu W. Liu M. Liu X. Chang CZ. Zhu H. Dong ZB. SynOpen 2017; 1: 1
    • 20d Zhu H. Liu X. Chang CZ. Dong ZB. Synthesis 2017; 49: 5211
    • 20e Dong ZB. Wang M. Zhu H. Liu X. Chang CZ. Synthesis 2017; 49: 5258
    • 20f Liu X. Cao Q. Xu W. Zeng MT. Dong ZB. Eur. J. Org. Chem. 2017; 5795
    • 20g Liu M. Zeng MT. Xu W. Wu L. Dong ZB. Tetrahedron Lett. 2017; 58: 4352
    • 20h Zeng MT. Xu W. Liu X. Chang CZ. Zhu H. Dong ZB. Eur. J. Org. Chem. 2017; 6060
    • 20i Xu W. Zeng MT. Liu SS. Li YS. Dong ZB. Tetrahedron Lett. 2017; 58: 4289
    • 21a Baars H. Beyer A. Kohlhepp SV. Bolm C. Org. Lett. 2014; 16: 536
    • 21b Beyer A. Reucher CM. M. Bolm C. Org. Lett. 2011; 13: 2876
    • 22a Minami H. Kanayama T. Tanaka R. Okamoto N. Sueda T. Yanada R. Eur. J. Org. Chem. 2016; 5990
    • 22b Arun V. Pilania M. Kumar D. Chem. Asian J. 2016; 11: 3345