7
80
Synlett
B. Movassagh, Z. Hosseinzadeh
Letter
References and Notes
(11) (a) Kumar, A.; Kumar, S. Tetrahedron 2014, 70, 1763. (b) Wang,
M.; Ren, K.; Wang, L. Adv. Synth. Catal. 2009, 351, 1568.
(1) (a) Trost, B. M.; Fleming, Ι. Comprehensive Organic Synthesis; Vol.
(c) Zheng, B.; Gong, Y.; Xu, H.-J. Tetrahedron 2013, 69, 5342.
6; Pergamon Press: New York, 1991. (b) Petraghani, N. In Tellu-
(
(
(
12) Li, Y.; Nie, C.; Wang, H.; Li, X.; Verpoort, F.; Duan, C. Eur. J. Org.
rium in Organic Synthesis; Katritzky, A. R.; Meth-Cohn, O.; Rees,
C. W., Eds.; Academic Press: San Diego, 1994. (c) Paulmier, C. I.
In Selenium Reagents and Intermediates in Organic Synthesis:
Organic Chemistry Series 4; Baldwin, J. E., Ed.; Pergamon Press:
Oxford, 1986. (d) Comasseto, J. V.; Barientos-Astigarraga, R. E.
Aldrichimica Acta 2000, 33, 66. (e) Thuillier, A. In Sulfur Reagents
in Organic Synthesis; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W.,
Eds.; Academic Press: San Diego, 1994.
Chem. 2011, 7331.
13) Prasad, Ch. D.; Balkrishna, S. J.; Kumar, A.; Bhakuni, B. S.;
Shrimali, K.; Biswas, S.; Kumar, S. J. Org. Chem. 2013, 78, 1434.
14) (a) Joshi-Pangu, A.; Ganesh, M.; Biscoe, M. R. Org. Lett. 2011, 13,
1
218. (b) Gong, H.; Gagne, M. R. J. Am. Chem. Soc. 2008, 130,
12177. (c) Aoyama, N.; Hamada, T.; Manabe, K.; Kobayashi, S.
J. Org. Chem. 2003, 68, 7329.
(
15) Zhao, L. X.; Moon, Y. S.; Basnet, A.; Kim, E.-K.; Jahng, Y.; Park, J.
G.; Jeong, T. C.; Cho, W.-J.; Choi, S.-U.; Lee, S.-Y.; Lee, C.-S.; Lee,
E. S. Bioorg. Med. Chem. Lett. 2004, 14, 1333.
(2) (a) Patai, S.; Rappoport, Z. The Chemistry of Organic Selenium
and Tellurium Compounds; Vol. 1; Wiley: New York, 1986.
(
b) Naddaka, V. I.; Sadekov, I. D.; Maksimenko, A. A.; Minkin, V.
I. Sulfur Rep. 1988, 8, 61. (c) Nicolaou, K. Tetrahedron 1981, 37,
097.
3) (a) Sarma, B. K.; Mugesh, G. Org. Biomol. Chem. 2008, 6, 965.
b) Nogueira, C. W.; Zeni, G.; Rocha, J. B. T. Chem. Rev. 2004, 104,
255. (c) Bonnet, B.; Soullez, D.; Girault, S.; Maes, L.; Landry, V.;
Davioud-Charret, E.; Sergheraert, C. Bioorg. Med. Chem. 2000, 8,
5. (d) Liu, G.; Link, J. T.; Pei, Z.; Reilly, E. B.; Leitza, S.; Nguyen,
(16) Wild, A.; Winter, A.; Schlütter, F.; Schubert, U. S. Chem. Soc. Rev.
2011, 40, 1459.
4
(
17) Park, J.; Pasupathy, A. N.; Goldsmith, J. I.; Chang, C.; Yaish, Y.;
Petta, J. R.; Rinkoski, M.; Sethna, J. P.; Abruña, H. D.; McEuen, P.
L.; Ralph, D. C. Nature (London) 2002, 417, 722.
(
(
6
(18) Winter, A.; Hager, M. D.; Newkome, G. R.; Schubert, U. S. Adv.
Mater. 2011, 23, 5728.
9
(19) Movassagh, B.; Yousefi, A.; Momeni, B. Z.; Heydari, S. Synlett
B.; Marsh, K. C.; Okasinsk, G. F.; Geldern, T. W. V.; Ormes, M.;
Fowler, K.; Gallatin, M. J. Med. Chem. 2000, 43, 4025. (e) Wang,
Y. G.; Chackalamannil, S.; Chang, W.; Greenlee, W.; Ruperto, V.;
Duffy, R. A.; McQuade, R.; Lachowicz, J. E. Bioorg. Med. Chem.
Lett. 2001, 11, 891.
2
014, 1385.
(
(
20) Wang, J.; Hanan, G. S. Synlett 2005, 1251.
21) General procedure for the preparation of diorgano chalco-
genides: A flame-dried test tube containing a magnetic stirring
bar was charged with diorgano dichalcogenide (0.5 mmol), aryl
halide (1.0 mmol), KOH (1.0 mmol), and anhydrous DMSO (2
mL) [for aryl bromides or chlorides, TBAB (1.0 mmol) was also
added]. Then, CuI (10 mol%) and Mtpy (10 mol%) were added to
the above mixture, and the reaction mixture was heated at
(
4) (a) Krief, A. In Comprehensive Organometallic Chemistry ΙΙ; Vol.
11; Chap. 13; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.;
Pergamon Press: New York, 1995. (b) Miyaura, N. In Metal Cata-
lyzed Cross-Coupling Reactions; Vol. 1; de Meijere, A.; Diederich,
F., Eds.; Wiley-VCH: Weinheim, 2004, 41–123. (c) Zeni, G.;
Ludtke, D. S.; Panatieri, R. B.; Braga, A. L. Chem. Rev. 2006, 106,
110 °C under nitrogen. The progress of the reaction was moni-
tored by TLC. Upon completion of the reaction, the mixture was
cooled to r.t., poured into H O (10 mL), and extracted with
EtOAc (3 × 8 mL). The combined organic layers were dried over
MgSO , filtered, and concentrated in vacuo to give the crude
product, which was further purified by preparative TLC (silica
gel; n-hexane–EtOAc, 9:1). The identities of the products were
confirmed by IR, H and C NMR spectroscopic analysis.
1032. (d) Perin, G.; Lenardao, E. J.; Jacob, R. G.; Panatieri, R. B.
2
Chem. Rev. 2009, 109, 1277.
(
5) (a) Gujadhur, R. K.; Venkataraman, V. Tetrahedron Lett. 2003, 44,
4
8
(
1. (b) Kwong, F. W.; Buchwald, S. L. Org. Lett. 2002, 4, 3517.
c) Suzuki, H.; Abe, H.; Osuka, A. Chem. Lett. 1981, 151. (d) Li, Y.;
Li, X.; Wang, H.; Chen, T.; Xie, Y. Synthesis 2010, 3602.
e) Mondal, J.; Modak, A.; Dutta, A.; Bhaumik, A. Dalton Trans.
011, 5228.
1
13
(
2
(
(
(
22) Haldón, E.; Álvarez, E.; Nicasio, M. C.; Pérez, P. Organometallics
2
009, 28, 3815.
23) Xu, H.-J.; Zhao, X.-Y.; Deng, J.; Fu, Y.; Feng, Y.-S. Tetrahedron Lett.
009, 50, 434.
(
6) (a) Movassagh, B.; Takallou, A.; Mobaraki, A. J. Mol. Catal. A:
Chem. 2015, 401, 55. (b) Itoh, T.; Mase, T. Org. Lett. 2004, 6,
2
4587. (c) Nishiyama, Y.; Tokunaga, K.; Sonada, N. Org. Lett. 1999,
1, 1725. (d) Correa, A.; Carril, M.; Balm, C. Angew. Chem. Int. Ed.
2008, 47, 2880.
24) (a) Yang, F.; Huifeng, W.; Fangfang, S.; Yaming, L.; Xinmei, F.;
Kun, J. Tetrahedron 2009, 65, 9737. (b) Fernandez-Rodriguez, M.
A.; Hartwig, J. F. J. Org. Chem. 2009, 74, 1664. (c) Zhang, J.;
Medley, C. M.; Krause, J. A.; Guan, H. Organometallics 2010, 29,
(
7) (a) Jammi, S.; Baruna, P.; Rout, L.; Saha, P.; Punniyamurty, T. Tet-
rahedron Lett. 2008, 44, 1484. (b) Zhang, Y.; Ngeow, K. C.; Ying, J.
Y. Org. Lett. 2007, 9, 3495.
8) Eichmann, C. C.; Stambuli, J. P. J. Org. Chem. 2009, 74, 4005.
9) (a) Wang, H.; Jiang, L.; Chen, T.; Li, Y. Eur. J. Org. Chem. 2010,
6
393. (d) Sang, B. L.; Jong-In, H. Tetrahedron Lett. 1995, 36, 8439.
e) Reddy, V. P.; Kumar, A. V.; Swapna, K.; Rao, K. R. Org. Lett.
009, 11, 951.
Di-p-tolyl Sulfide
(
2
(
(
2
(
6
324. (b) Chatterjee, T.; Ranu, B. C. J. Org. Chem. 2013, 78, 7145.
c) Li, Y.; Wang, H.; Li, X.; Chen, T.; Zhao, D. Tetrahedron 2010,
6, 8583. (d) Reddy, V. P.; Kumar, A. V.; Swapna, K.; Rao, K. R.
1
White solid; mp 55–57 °C; H NMR (300 MHz, CDCl ): δ = 7.30
3
13
(d, J = 8.4 Hz, 4 H), 7.16 (d, J = 8.4 Hz, 4 H), 2.38 (s, 6 H); C NMR
(
75.5 MHz, CDCl ): δ = 136.9, 132.7, 131.1, 130.0, 21.1.
3
Org. Lett. 2009, 11, 951. (e) Singh, D.; Alberto, E. E.; Rodrigues, O.
E. D.; Braga, A. L. Green Chem. 2009, 11, 1521. (f) Taniguchi, N.;
Onami, T. J. Org. Chem. 2004, 69, 915. (g) Kumar, S.; Engman, L.
J. Org. Chem. 2006, 71, 5400. (h) Kumar, A.; Bhakuni, B. S.;
Prasad, Ch. D.; Kumar, Sh.; Kumar, S. Tetrahedron 2013, 69,
4
-Methoxyphenyl Phenyl Sulfide
1
Colorless oil; H NMR (300 MHz, CDCl ): δ = 7.49 (dt, J = 6.9,
3
1
3
1
.8 Hz, 2 H), 7.19–7.29 (m, 5 H), 6.96 (dt, J = 6.9, 1.8 Hz, 2 H),
.85 (s, 3 H); C NMR (75.5 MHz, CDCl ): δ = 159.8, 138.6,
35.3, 128.9, 128.2, 125.7, 124.3, 115.0, 55.3.
13
3
5
383.
10) Kundu, D.; Ahammed, S.; Ranu, B. C. Green Chem. 2012, 14,
024.
Naphthalen-2-yl p-Tolyl Sulfide
White solid; mp 69–71 °C; H NMR (300 MHz, CDCl ): δ = 7.75–
(
1
3
2
7.86 (m, 4 H), 7.41–7.52 (m, 5 H), 7.21 (d, J = 9.0 Hz, 2 H), 2.42
©
Georg Thieme Verlag Stuttgart · New York — Synlett 2016, 27, 777–781