Communication
RSC Advances
1
H NMR (CDCl
3
, 300 MHz): d ¼ 7.27–7.47 (m, 8H).
3 (a) T. M. Postma and F. Albericio, Eur. J. Org. Chem., 2014,
2014, 3519; (b) J. L. G. Ruano, A. Parra and J. Aleman,
Green Chem., 2008, 10, 706; (c) L. Zhang, C. P. Chou and
M. Moo-Young, Biotechnol. Adv., 2011, 29, 923; (d)
S. A. Caldarelli, M. Hamel, J. F. Duckert, M. Ouattara,
M. Calas, M. Maynadier, S. Wein, C. P ´e rigaud, A. Pellet,
H. J. Vial and S. Peyrottes, J. Med. Chem., 2012, 55, 461.
+
MS (EI, m/z): 470 [M ].
Diphenyl disulde (Table 2, entry 17). The product was ob-
tained (ethyl acetate/n-hexane, 1 : 20) as a yellow solid in 98%
yield. Mp ¼ 58–61 C. GC-mass (EI): m/z ¼ 314.0 [M ].
ꢀ
+
Conclusions
4
(a) G. Pettenden and A. Shuker, J. Chem. Soc., Perkin Trans. 1,
992, 1215; (b) C. S. Sevier and C. A. Kaiser, Nat. Rev. Mol. Cell
1
In summary, a novel, effective and one-pot procedure was
developed for the direct synthesis of dichalcogenides from
various aryl halides (and –OTs) and sulphur or selenium in PEG.
The important feature of this method is using MOF-199 as
a recyclable, porous and chemoselective catalyst. This protocol
has several advantages: normal atmospheric conditions, the use
of a few amount of catalyst, ligand-free systems, an easily
available and low cost reagents, faint order procedure and the
reactions can be carried out in PEG as green solvent instead of
the usually used organic solvents.
Biol., 2002, 3, 836.
5
6
K. D. Lee, G. Saito and J. A. Swanson, Adv. Drug Delivery Rev.,
2003, 55, 199.
M. Ibrahim, W. Hassan, D. F. Meinerz, M. Santos,
C. Klimaczewski, A. Deobald, M. S. Costa, C. W. Nogueira,
N. B. V. Barbosa and J. B. T. Rocha, Mol. Cell. Biochem.,
2012, 371, 97.
7
8
L. Savegnago, Environ. Toxicol. Pharmacol., 2006, 21, 86.
(a) C. W. Nogueira, G. Zeni and J. B. T. Rocha, Chem. Rev.,
2004, 104, 6255; (b) L. Savegnago, Eur. J. Pharmacol., 2007,
555, 129.
Acknowledgements
9 K. Prabhu and S. Chandrasekaran, Chem. Commun., 1997,
021.
0 (a) L. Syper and J. Miochowski, Tetrahedron, 1988, 44, 6119;
b) A. Krief, C. Delmotte and C. Colaux-Castillo, Pure Appl.
1
We acknowledge the nancial support of Ilam University
Research Council.
1
(
Chem., 2000, 72, 1709; (c) A. Krief, W. Dumont and
C. Delmotte, Angew. Chem., Int. Ed., 2000, 39, 1669.
1 P. Salama and C. Bernard, Tetrahedron Lett., 1995, 36, 5711.
Notes and references
1
1
(a) Y. Nishiyama, K. Maehira, J. Nakase and N. Sonoda, 12 (a) N. Taniguchi, Synlett, 2005, 1687; (b) N. Taniguchi,
Tetrahedron Lett., 2005, 46, 7415; (b) N. Taniguchi, J. Org.
Chem., 2007, 72, 1241; (c) S.-I. Fukuzawa, E. Shimizu,
Y. Atsuumi, M. Haga and K. Ogata, Tetrahedron Lett., 2009,
Tetrahedron, 2012, 68, 10510; (c) Z. Li, F. Ke, H. Deng,
H. Xu, H. Xianga and X. Zhou, Org. Biomol. Chem., 2013,
11, 2943; (d) M. Z. Kassaee, E. Motamedi, B. Movassagh
and S. Poursadeghi, Synthesis, 2013, 45, 2337; (e) D. Singh,
A. M. Deobald, L. R. S. Camargo, G. Tabarelli,
O. E. D. Rodrigues and A. L. Braga, Org. Lett., 2010, 12, 3288.
50, 2374; (d) D. Alves, R. G. Lara, M. E. Contreira,
E. S. Radatz, L. F. B. Duarte and G. Perin, Tetrahedron Lett.,
2
1
012, 53, 3364; (e) N. Taniguchi, J. Org. Chem., 2015, 80,
764; (f) D. Alves, R. G. Lara, M. E. Contreira, E. S. Radatz, 13 (a) S. Kumar and L. Engman, J. Org. Chem., 2006, 71, 5400; (b)
L. F. B. Duarte and G. Perin, Tetrahedron Lett., 2012, 53,
S. M. S. Chauhan, A. Kumar and K. A. Srinivas, Chem.
Commun., 2003, 2348; (c) V. Jamier, L. A. Ba and C. Jacob,
Chem.–Eur. J., 2010, 16, 10920; (d) Y. S. Feng, H. X. Qi,
W. C. Wang, Y. F. Liang and H. J. Xu, Tetrahedron Lett.,
2012, 53, 2914; (e) Y. F. Liang and H. J. Xu, Tetrahedron
Lett., 2012, 53, 2914; (f) L. Capella, P. C. Montevecchi and
D. Nanni, J. Org. Chem., 1994, 59, 3368.
3
2
364; (g) B. Movassagh and M. Navidi, Tetrahedron Lett.,
008, 49, 6712; (h) T. Chatterjee and B. C. Ranu, J. Org.
Chem., 2013, 78, 7145; (i) V. P. Raddy, A. V. Kumar,
K. Swapna and K. R. Rao, Org. Lett., 2009, 11, 951; (j)
C. He, X. Qian and P. Sun, Org. Biomol. Chem., 2014, 12,
6072; (k) A. J. Mukherjee, S. S. Zade, H. B. Singh and
R. B. Sunoj, Chem. Rev., 2010, 110, 4357.
14 (a) B. Mandal and B. Basu, RSC Adv., 2014, 4, 13854; (b)
D. Witt, Synthesis, 2008, 16, 2491; (c) L. Khanna,
P. Khanna, C. S. Panda and S. Panda, Mini-Rev. Org. Chem.,
2013, 10, 268.
2
(a) R. J. Cremlyn, An Introduction to Organo-Sulfur Chemistry,
Wiley & Sons, New York, 1996; (b) I. Shcherbakova and
A. F. Pozharskii, in Comprehensive Organic Functional Group
Transformations II, ed. A. R. Katritzky, R. Taylor and Ch. 15 (a) J. T. Reeves, K. Camara, Z. S. Han, Y. Xu, H. Lee,
Ramsden, Pergamon, Oxford, 2004, vol. 2, p. 210; (c)
A. Satyam, M. D. Hocker, K. A. Kane-Maguire,
A. S. Morgan, H. O. Villar and M. H. Lyttle, J. Med. Chem.,
C. A. Busacca and C. H. Senanayake, Org. Lett., 2014, 16,
1196; (b) Z. Qiao, J. Wei and X. Jiang, Org. Lett., 2014, 16,
1212; (c) H. Firouzabadi, N. Iranpoor and M. Abbasi,
Tetrahedron Lett., 2010, 51, 508; (d) K. H. V. Reddy,
V. P. Reddy, J. Shankar, B. Madhav, B. S. P. A. Kumar and
Y. V. D. Nageswar, Tetrahedron Lett., 2011, 52, 2679; (e)
C. B. Kelly, C. Lee and N. E. Leadbeater, Tetrahedron Lett.,
2011, 52, 4587; (f) D. W. Emerson, B. L. Bennett and
S. M. Steinberg, Synth. Commun., 2005, 35, 631; (g) F. Ke,
1996, 39, 1736; (d) A. L. Braga, E. E. Alberto, L. C. Soares,
J. B. T. Rocha, J. H. Sudati and D. H. Roos, Org. Biomol.
Chem., 2009, 7, 43; (e) G. Mugesh, A. Panda, H. B. Singh,
N. S. Punekar and R. J. Butcher, Chem. Commun., 1998,
2227; (f) G. Mugesh, A. Panda, H. B. Singh, N. S. Punekar
and R. J. Butcher, J. Am. Chem. Soc., 2001, 123, 839; (g)
M. Iwaoka and S. Tomoda, J. Am. Chem. Soc., 1994, 116, 2557.
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