Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2015; 47(23): 3741-3745
DOI: 10.1055/s-0035-1560458
DOI: 10.1055/s-0035-1560458
paper
Copper Nanoparticle Catalyzed Formation of C–S Bonds through Activation of S–S and C–H Bonds: An Easy Route to Alkynyl Sulfides
Authors
Further Information
Publication History
Received: 10 May 2015
Accepted after revision: 16 July 2015
Publication Date:
21 August 2015 (online)
Abstract
An efficient method for copper nanoparticle catalyzed ligand-free S–Csp bond formation was developed by using dimethyl sulfoxide as the solvent, a base, and molecular oxygen as a green oxidant. This study provides a new catalytic route for the production of alkynyl sulfides through dual activation of S–S and C–H bonds. A wide range of alkynyl sulfides were synthesized on a large scale with a low catalyst loading (0.5 mol% Cu). This synthetic methodology could also be extended to selenides, whereas tellurides underwent analogous reactions in the absence of a catalyst.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560458.
- Supporting Information (PDF) (opens in new window)
-
References
- 1 Gridnev ID, Miyaura N, Suzuki A. J. Org. Chem. 1993; 58: 5351
- 2 Zhu G, Kong W, Feng H, Qian Z. J. Org. Chem. 2014; 79: 1786
- 3 Savarin C, Srogl J, Liebeskind LS. Org. Lett. 2001; 3: 91
- 4 Gerard J, Hevesi L. Tetrahedron 2004; 60: 367
- 5 Mantovani AC, Back DF, Zeni G. Eur. J. Org. Chem. 2012; 4574
- 6 Dabdoub MJ, Begnini ML, Guerrero PG. Jr. Tetrahedron 1998; 54: 2371
- 7 Morzherin Y, Prokhorova PE, Musikhin DA, Glukhareva TV, Fain Z. Pure Appl. Chem. 2011; 83: 715
- 8 Oura I, Shimizu K, Ogata K, Fukuzawa S. Org. Lett. 2010; 12: 1752
- 9 Ding S, Jia G, Sun J. Angew. Chem. Int. Ed. 2014; 53: 1877
- 10 Marcelo G, Ricardo EW, Frizon TE, Rocha MS. T, Singh D, Paixao MW, Braga AL. Tetrahedron 2012; 68: 10426
- 11 Godoi M, Liz DG, Ricardo EW, Rocha MS. T, Azeredo JB, Braga AL. Tetrahedron 2014; 70: 3349
- 12 Tingoli M, Tiecco M, Testaferri L, Temperini A. Tetrahedron 1995; 51: 4691
- 13 Das JP, Roy UK, Roy S. Organometallics 2005; 24: 6136
- 14 Ahammad S, Bhadra S, Kundu D, Ranu BC. Tetrahedron 2012; 68: 10542
- 15 Lara RG, Rosa PC, Soares LK, Silva MS, Jacob RG, Perin G. Tetrahedron 2012; 68: 10414
- 16 Movassagh B, Navidi M. Chin. Chem. Lett. 2012; 23: 1035
- 17 Rampon DS, Giovenardi R, Silva RL, Rambo RS, Merlo AA, Schneider PH. Eur. J. Org. Chem. 2011; 7066
- 18 Sharma A, Schwab RS, Braga AL, Barcellos T, Paixao MW. Tetrahedron Lett. 2008; 49: 5172
- 19 Zou KB, Qiu RH, Fang DW, Liu XY, Xu XH. Synth. Commun. 2008; 38: 2237
- 20 Bieber LW, Da Silva MF, Menezes PH. Tetrahedron Lett. 2004; 45: 2735
- 21 Yang Y, Dong W, Guo Y, Rioux RM. Green Chem. 2013; 15: 3170
- 22 Fihri A, Bouhara M, Nekoueishahraki B, Basset J.-M, Polshettiwar V. Chem. Soc. Rev. 2011; 40: 5181
- 23 Cuenya BR. Acc. Chem. Res. 2013; 46: 1682
- 24 Gawande MB, Branco PS, Varma RS. Chem. Soc. Rev. 2013; 42: 3371
- 25 Zhang Z, Xu B, Wang X. Chem. Soc. Rev. 2014; 43: 7870
- 26 Woo H, Mohan B, Heo E, Park JC, Song H, Park KH. Nanoscale Res. Lett. 2013; 8: 390
- 27 Zolfigol MA, Khakyzadeh V, Zare AR. M, Rostami A, Zare A, Iranpoor N, Beyzavi MH, Luque R. Green Chem. 2013; 15: 2132
- 28 Zamani F, Hosseini SM, Kianpour S. Solid State Sci. 2013; 26: 139
- 29 Mohan B, Woo H, Jang S, Lee S, Park S, Park KH. Solid State Sci. 2013; 22: 16
- 30 Mohan B, Kang H, Park KH. Inorg. Chem. Commun. 2013; 35: 239
- 31 Mohan B, Hwang S, Woo H, Park KH. Tetrahedron 2014; 70: 2699
- 32 Mohan B, Hwang S, Jang S, Park KH. Synlett 2014; 25: 2078
- 33 Mohan B, Yoon C, Jang S, Park KH. ChemCatChem 2015; 7: 405
- 34 Millward AR, Yaghi OM. J. Am. Chem. Soc. 2005; 127: 17998
- 35 Radatz CS, Soares LA, Vieira ER, Alves D, Russowsky D, Schneider PH. New J. Chem. 2014; 38: 1410
- 36 Movassagh B, Yousefi A, Momeni BZ, Heydari S. Synlett 2014; 25: 1385