P.-S. Luo et al. / Tetrahedron Letters 50 (2009) 1066–1070
1069
Table 2 (continued)
Entry
Disulfide 1
R02
Product
Yieldb (%)
S
S
15
(2a)
36 (17)
S
N
N
N
(1l)
S
S
16c
(2a)
Trace (18)
S
(1m)
a
Reaction conditions: 1 (0.3 mmol), 2 (0.9 mmol), CuI (5 mol %), L5 (10 mol %), and TBAFꢀ3H2O (3 equiv) at 100 °C for 24 h.
Isolated yield based on disulfide 1.
b
F
References and notes
TBAF
ArSi(OMe)3
Ar Si(OMe)3
2
1. (a) Buntain, I. G.; Hatton, L. R.; Hawkins, D. W.; Pearson, C. J.; Roberts, D. A. Eur.
Pat. Appl. 295,117 A1, 1988; Chem. Abstr. 1990, 112, 35845n).; (b) Wu. T.-T. US
patent 5,814,652, 1998; Chem. Abstr. 1998, 129, 256473.; (c) Caboni, P. ;
Sammelson, R. E.; Casida, J. E. J. Agric. Food Chem. 2003, 24, 7055; (d) Wang, Y.;
Chackalamannil, S.; Hu, Z.; Clader, J. W.; Greenlee, W.; Billard, W.; Binch, H., III;
Crosby, G.; Ruperto, V.; Duffy, R. A.; McQuade, R.; Lachowicz, J. Bioorg. Med.
Chem. Lett. 2000, 10, 2247; (e) Nielson, S. F.; Nielson, E. O.; Olsen, G. M.;
Liljefors, T.; Peters, D. J. Med. Chem. 2000, 43, 2217; (f) De Martino, G.; Edler, M.
C.; La Regina, G.; Cosuccia, A.; Barbera, M. C.; Barrow, D.; Nicholson, R. I.;
Chiosis, G.; Brancale, A.; Hamel, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2006,
49, 947.
A
CuII
F
L
Ar Si(OMe)3
ArSAr'
air + X-
CuIILn
A
FSi(OMe)3, I-
B
Ar'CuILn
ArS
Ar'
CuIILn
C
ArSSAr
F
2. (a) Metzner, P.; Thuillier, A. In Sulfur Reagents in Organic Synthesis; Katritzky, A.
R., Meth-Cohn, O., Rees, C. W., Eds.; Academic Press: San Diego, 1994; (b)
Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205; (c) Ley, S. V.; Thomas, A. W.
Angew. Chem., Int. Ed. 2003, 42, 5400.
1
FSi(OMe)3, I-
ArSAr'
ArS CuILn
ArS
F
CuIILn
3. (a) Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 13; (b) Suzuki, H.;
Abe, H.; Osuka, A. Chem. Lett. 1980, 1363; (c) Bowman, W. R.; Heaney, H.;
Smith, P. H. G. Tetrahedron Lett. 1984, 25, 5821; (d) Ciattini, P. G.; Morera, E.;
Ortar, G. Tetrahedron Lett. 1995, 36, 4133; (e) Zheng, N.; Mcwilliams, C.;
Fleitz, F. J.; Armstrong, J. D.; Volante, R. P. J. J. Org. Chem. 1998, 63, 9606; (f)
Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803; (g)
Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517; (h) Bates, C. G.;
Saejueng, P.; Doherty, M. Q.; Venkataraman, D. Org. Lett. 2004, 6, 5005; (i)
Deng, W.; Zou, Y.; Wang, Y.-F.; Liu, L.; Guo, Q.-X. Synlett 2004, 1254; (j)
Gendre, F.; Yang, M.; Diaz, P. Org. Lett. 2005, 7, 2719; (k) Zheng, Y.; Du, X.;
Bao, W. Tetrahedron Lett. 2006, 47, 1217; (l) Zhu, D.; Xu, L.; Wu, F.; Wan, B.
Tetrahedron Lett. 2006, 47, 5781; (m) Chen, Y.-J.; Chen, H.-H. Org. Lett. 2006,
8, 5609; (n) Wang, Z.; Mo, H.; Bao, W. Synlett 2007, 91; (o) Lv, X.; Bao, W. J.
Org. Chem. 2007, 72, 3863; (p) Kabir, M. S.; Van Linn, M. L.; Monte, A.; Cook,
J. M. Org. Lett. 2008, 10, 3363; (q) Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587;
(r) Sperotto, E.; van Klink, G. P. M.; de Vries, J. G.; van Koten, G. J. Org. Chem.
2008, 73, 5625; (s) Zhang, Y.; Ngeow, K. C.; Ying, J. Y. Org. Lett. 2007, 9,
3495; (t) Wong, Y.-C.; Jayanth, T. T.; Cheng, C.-H. Org. Lett. 2006, 8, 5613; (u)
Lee, J.-Y.; Lee, P. H. J. Org. Chem. 2008, 73, 7413; (v) Correa, A.; Carril, M.;
Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 2880; (w) Carril, M.; SanMartin, R.;
Domínguez, E.; Tellitu, I. Chem. Eur. J. 2007, 13, 5100.
4. (a) Chowdhury, S.; Roy, S. Tetrahedron Lett. 1997, 38, 2149; (b) Kundu, A.; Roy,
S. Organometallics 2000, 19, 105; (c) Nishino, T.; Okada, M.; Kuroki, T.;
Watanabe, T.; Nishiyama, Y.; Sonoda, N. J. Org. Chem. 2002, 67, 8696; (d)
Nishino, T.; Nishiyama, Y.; Sonoda, N. Chem. Lett. 2003, 928; (e) Ranu, B. C.;
Mandal, T. J. Org. Chem. 2004, 69, 5793; (f) Ajiki, K.; Tanaka, K. Org. Lett. 2005, 7,
4193; (g) Kumar, S.; Engman, L. J. Org. Chem. 2006, 71, 5400; (h) Millois, C.;
Diaz, P. Org. Lett. 2000, 2, 1705; (i) Taniguchi, N.; Onami, T. Synlett 2003, 829; (j)
Taniguchi, N.; Onami, T. J. Org. Chem. 2004, 69, 915; (k) Taniguchi, N. J. Org.
Chem. 2004, 69, 6904; (l) Taniguchi, N. Synlett 2005, 1687.
D
Ar Si(OMe)3
X
air + X-
E
A
Scheme 2. A working mechanism.
intermediate F. Finally, reductive elimination of intermediate F
takes place to afford the target product and regenerate the active
Cu(I) species. We deduced that ligand L5 displayed the highest
activity due to its steric and electronic effects. Study on the real
role of ligand is in progress.
In summary, we describe here the first example of the syn-
thesis of diarysulfides by the copper-catalyzed oxidative S-ary-
lation of 1,2-diaryldisulfides with aryltrimethoxysilanes. In the
presence of CuI, 2-(di-tert-butylphosphino)biphenyl, and TBAF
(n-Bu4NF), a variety of 1,2-diaryldisulfides underwent the S-
arylation reaction with aryltrimethoxysilanes smoothly to af-
ford the corresponding products in moderate to good yield.
Noteworthy is that the reaction is conducted under solvent-
free conditions. Further application of the present system in
organic synthesis and study of the detailed mechanism are
underway.
5. (a) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019; (b)
Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309; (c) Prokopcova, H.;
Kappe, C. O. J. Org. Chem. 2007, 72, 4440.
Acknowledgments
6. (a) Miyaura, N.. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A.,
Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 1, pp 41–123; (b)
Taniguchi, N. Synlett 2006, 1351; (c) Taniguchi, N. J. Org. Chem. 2007, 72, 1241.
7. (a) Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 53, 918; (b) Hatanaka, Y.; Goda,
K.; Hiyama, T. J. Organomet. Chem. 1994, 465, 97.
8. For reviews, see: (a) Diederich, F.; Stang, P. J. Metal-catalyzed Cross-coupling
Reactions; Wiley-VCH: Weinheim, 1998; (b) Miyaura, N. Cross-Coupling
Reaction; Springer: Berlin, 2002; (c) de Meijere, A.; Diederich, F. Metal-
Catalyzed Cross-coupling Reactions; Wiley-VCH: Weinheim, 2004.
The authors thank the Zhejiang Provincial Natural Science
Foundation of China (Nos. Y407116 and Y4080169), National Nat-
ural Science Foundation of China (Nos. 20872112 and 20572020),
and Foundation of Wenzhou University (2007L004) for financial
support.
9. (a) Liang, Y.; Xie, Y.-X.; .Li, J.-H. J. Org. Chem. 2006, 71, 379; (b) Deng, C.-L.; Xie,
Y.-X.; Yin, D.-L. Li; J.-H. Synthesis 2006, 3370; (c) Xie, Y.-X.; Deng, C.-L.; Pi, S.-F.;
Li, J.-H.; Yin, D.-L. Chin. J. Chem. 2006, 24, 1290; (d) Xie, Y.-X.; Pi, S.-F.; Wang, J.;
Yin, D.-L.; Li, J.-H. J. Org. Chem. 2006, 71, 8324; (e) Li, J.-H.; Deng, C.-L.; Xie, Y.-X.
Synthesis 2006, 969; (f) Song, R.-J.; Deng, C.-L.; Xie, Y.-X.; Li, J.-H. Tetrahedron
Supplementary data
Supplementary data associated with this article can be found, in