Environmentally Friendly and Recyclable CuCl2-Mediated C–S Bond Coupling Strategy Using DMEDA as Ligand, Base, and Solvent

Guodong Shen; Qichao Lu; Zeyou Wang; Weiwei Sun; Yalin Zhang; Xianqiang Huang; Manman Sun; Zhiming Wang

doi:10.1055/a-1561-5508

Synthesis, Table of Contents

Synthesis 2022; 54(01): 184-198
DOI: 10.1055/a-1561-5508

paper

Environmentally Friendly and Recyclable CuCl₂-Mediated C–S Bond Coupling Strategy Using DMEDA as Ligand, Base, and Solvent

Guodong Shen∗

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China

,

Qichao Lu

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China

,

Zeyou Wang

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China

,

Weiwei Sun

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China

,

Yalin Zhang

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China

,

Xianqiang Huang∗

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China

,

Manman Sun

^bAdvanced Research Institute and Department of Chemistry, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, Zhejiang, P. R. of China

,

Zhiming Wang

^bAdvanced Research Institute and Department of Chemistry, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, Zhejiang, P. R. of China

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Abstract

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Abstract

Simple reaction conditions and recyclable reagents are crucial for environmentally friendly industrial applications. An environment-friendly, recyclable and economic strategy was developed to synthesize diaryl chalcogenides by the CuCl₂-catalyzed C–S bond-formation reaction via iodobenzenes and benzenethiols/1,2-diphenyldisulfanes using N,N′-dimethylethane-1,2-diamine (DMEDA) as ligand, base, and solvent. For these reactions, especially the reactions of diiodobenzenes and aminobenzenethiols/disulfanediyldianilines, a range of substrates are compatible and give the corresponding products in good to excellent yields. Both of the reagents in the catalytic system (CuCl₂/DMEDA) are inexpensive, conveniently separable, and recyclable for more than five cycles.

Key words

environment friendly - recyclable - C–S bond coupling - DMEDA - CuCl₂

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References

References

1a Rathore V, Kumar S. Green Chem. 2019; 21: 2670
1b Wang YQ, Deng JD, Chen JH, Cao F, Hou YS, Yang YH, Deng XM, Yang JR, Wu LX, Shao XF, Shi T, Wang Z. ACS Catal. 2020; 10: 2707

2a Engman L, Stern D, Frisell H, Vessman K, Berglund M, Ek B, Andersson CM. Bioorg. Med. Chem. 1995; 3: 1255
2b Amorati R, Pedulli GF, Valgimigli L, Johansson H, Engman L. Org. Lett. 2010; 12: 2326
2c De Martino G, Edler MC, LaRegina G, Cosuccia A, Barbera MC, Barrow D, Nicholson RI, Chiosis G, Brancale A, Hamel E, Artico M, Silvestri R. J. Med. Chem. 2006; 49: 947

3 Bierbeek AV, Gingras M. Tetrahedron Lett. 1998; 39: 6283
4 Kondo T, Mitsudo TA. Chem. Rev. 2000; 100: 3205

5a Guo SR, Yuan YQ, Xiang JN. Org. Lett. 2013; 15: 4654
5b Sujatha A, Thomas AM, Thankachan AP, Anilkumar G. ARKIVOC 2015; (i): 1-28
5c Panigrahi R, Sahu SK, Behera PK, Panda S, Rout L. Chem. Eur. J. 2020; 26: 620
5d Migita T, Shimizu T, Asami Y, Shiobara J, Kato Y, Kosugi M. Bull. Chem. Soc. Jpn. 1980; 53: 1385

6 Swapna K, Murthy SN, Jyothi MT, Nageswar YV. D. Org. Biomol. Chem. 2011; 9: 5989

7a Rojas AJ, Pentelute BL, Buchwald SL. Org. Lett. 2017; 19: 4263
7b Fernandez-Rodriguez MA, Hartwig JF. Chem. Eur. J. 2010; 16: 2355
7c Fernandez-Rodríguez MA, Shen Q, Hartwig JF. J. Am. Chem. Soc. 2006; 128: 2180
7d Xu J, Liu RY, Yeung CS, Buchwald SL. ACS Catal. 2019; 9: 6461
7e Murata M, Buchwald SL. Tetrahedron 2004; 60: 7397
7f Li GY. Angew. Chem. Int. Ed. 2001; 40: 1513
7g Guo SR, He WM, Xiang JN, Yuan YQ. Chem. Commun. 2014; 50: 8578

8 Samuel DT, Christopher JP, Oleg VO. J. Am. Chem. Soc. 2014; 136: 14772
9 Wong YC, Jayanth TT, Cheng CH. Org. Lett. 2006; 8: 5613

10a Jouffroy M, Kelly CB, Molander GA. Org. Lett. 2016; 18: 876
10b Oderinde MS, Frenette M, Robbins DW, Aquila B, Johannes JW. J. Am. Chem. Soc. 2016; 138: 1760
10c Zhang Y, Ngeow YK. C, Ying JY. Org. Lett. 2007; 9: 3495
10d Sikari R, Sinha S, Das S, Saha S, Chakraborty G, Mondal R, Paul ND. J. Org. Chem. 2019; 84: 4072
10e Jones KD, Power DJ, Bierer D, Gericke KM, Stewart SG. Org. Lett. 2018; 20: 208
10f Kashin AS, Degtyareva ES, Eremin DB, Ananikov VP. Nat. Commun. 2018; 9: 2936
10g Qin YZ, Sun R, Gianoulis NP, Nocera DG. J. Am. Chem. Soc. 2021; 143: 2005
10h Yu TY, Pang HB, Cao YL, Gallou F, Lipshutz BH. Angew. Chem. Int. Ed. 2021; 60: 3708

11a Bhunia S, Pawar GG, Kumar SV, Jiang Y, Ma D. Angew. Chem. Int. Ed. 2017; 56: 16136
11b Larsson PF, Correa A, Carril M, Norrby PO, Bolm C. Angew. Chem. Int. Ed. 2009; 48: 5691
11c Bates CG, Saejueng P, Doherty MQ, Venkataraman D. Org. Lett. 2004; 6: 5005
11d Sperotto E, van Klink GP. M, de Vries JG, van Koten GL. J. Org. Chem. 2008; 73: 5625
11e Rout L, Sen TK, Punniyamurthy T. Angew. Chem. Int. Ed. 2007; 46: 5583
11f Kajiwara R, Takamatsu K, Hirano K, Miura M. Org. Lett. 2020; 22: 5915
11g Yarmohammadi N, Ghadermazi M, Mozafari R. RSC Adv. 2021; 11: 9366

12 Correa A, Carril M, Bolm C. Angew. Chem. Int. Ed. 2008; 47: 2880

13a Baldovino-Pantaleón O, Hernández-Ortega S, Reyes-Martínez R, Morales-Morales D. Adv. Synth. Catal. 2006; 348: 236
13b Kawamoto T, Kuma H, Kushi Y. Chem. Commun. 1996; 2121
13c Taniguchi N. J. Org. Chem. 2004; 69: 6904

For representative reviews, see:

14a Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
14b Carril M, SanMartin R, Dominguez E. Chem. Soc. Rev. 2008; 37: 639
14c Wu XF, Neumann H, Beller M. Chem. Rev. 2013; 113: 1

15a Evano G, Blanchard N, Toumi M. Chem. Rev. 2008; 108: 3054
15b Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2008; 47: 3096
15c Cho SH, Kim JY, Kwak J, Chang S. Chem. Soc. Rev. 2011; 40: 5068
15d Surry DS, Buchwald SL. Chem. Sci. 2010; 1: 13
15e Monniers F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954
15f Ma DW, Cai Q. Acc. Chem. Res. 2008; 41: 1450
15g Dai W, Shi H, Zhao X, Cao S. Org. Lett. 2016; 18: 4284
15h Ke J, Tang Y, Yi H, Li Y, Cheng Y, Liu C, Lei A. Angew. Chem. Int. Ed. 2015; 54: 6604

16 Shen GD, Yang BC, Huang XQ, Hou YX, Gao H, Cui JC, Cui CS, Zhang TX. J. Org. Chem. 2017; 82: 3798
17 Li F, Meng QQ, Chen HS, Li ZM, Wang QR, Tao FG. Synthesis 2005; 1305
18 Szmant HH, Segedi J, Dudek J. J. Org. Chem. 1953; 18: 745
19 Burger A, Stanmyer JL. J. Org. Chem. 1956; 21: 1382
20 Taniguchi N, Onami T. J. Org. Chem. 2004; 69: 915

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