R. T. Baker, A. Decken and S. A. Westcott, Tetrahedron Lett.,
2004, 45, 8493; (g) K. C. Nicolaou, A. E. Koumbis, S. A. Snyder
and K. B. Simonsen, Angew. Chem., Int. Ed., 2000, 39, 2529;
(h) M. Madesclaire, Tetrahedron, 1988, 44, 6537.
4 (a) P. Stanetty, H. Koller and M. Mihovilovic, J. Org. Chem.,
1992, 57, 6833; (b) P. F. Ranken and B. G. McKinnie, J. Org.
Chem., 1989, 54, 2985; (c) Y. Fort and A. L. Rodriguez, J. Org.
Chem., 2003, 68, 4918; (d) S. A. Pratt, M. P. Goble,
M. J. Mulvaney and P. G. M. Wuts, Tetrahedron Lett., 2000,
41, 3559.
5 Y. Jiang, Y. Qin, S. Xie, X. Zhang, J. Dong and D. Ma, Org. Lett.,
2009, 11, 5250.
6 (a) M. A. Fernandez-Rodrıguez, Q. Shen and J. F. Hartwig, J. Am.
Chem. Soc., 2006, 128, 2180; (b) E. Alvaro and J. F. Hartwig,
J. Am. Chem. Soc., 2009, 131, 7858; (c) C. S. Bryan, J. A. Braunger
and M. Lautens, Angew. Chem., Int. Ed., 2009, 48, 7064;
(d) A. Correa, M. Carril and C. Bolm, Angew. Chem., Int. Ed.,
2008, 47, 2880; (e) T. Itoh and T. Mase, Org. Lett., 2004, 6, 4587;
(f) M. S. Kabir, M. L. van Linn, A. Monte and J. M. Cook, Org.
Lett., 2008, 10, 3363; (g) C. Millois and P. Diaz, Org. Lett., 2000,
2, 1705; (h) C. G. Bates, P. Saejueng, M. Q. Doherty and
D. Venkataraman, Org. Lett., 2004, 6, 5005; (i) C. Savarin,
J. Srogl and L. S. Liebeskind, Org. Lett., 2002, 4, 4309;
(j) Y.-J. Chen and H.-H. Chen, Org. Lett., 2006, 8, 5609;
(k) B. C. Ranu, A. Saha and R. Jana, Adv. Synth. Catal., 2007,
349, 2690; (l) S. V. Ley and A. W. Thomas, Angew. Chem., Int. Ed.,
2003, 42, 5400; (m) L. Rout, T. K. Sen and T. Punniyamurthy,
Angew. Chem., Int. Ed., 2007, 46, 5583; (n) Y.-C. Wong,
T. T. Jayanth and C.-H. Cheng, Org. Lett., 2006, 8, 5613;
(o) V. Prakash Reddy, A. Vijay Kumar, K. Swapna and
K. Rama Rao, Org. Lett., 2009, 11, 1697; (p) V. Prakash Reddy,
K. Swapna, A. Vijay Kumar and K. Rama Rao, J. Org. Chem.,
2009, 74, 3189; (q) C. G. Bates, R. K. Gujadhur and D. Venkataraman,
Org. Lett., 2002, 4, 2803; (r) M. Murata and S. L. Buchwald,
Tetrahedron, 2004, 60, 7397; (s) F. Y. Kwong and S. L. Buchwald,
Org. Lett., 2002, 4, 3517.
7 (a) X. Chen, X.-S. Hao, C. E. Goodhue and J.-Q. Yu, J. Am.
Chem. Soc., 2006, 128, 6790; (b) X. Zhao, E. Dimitrijevic and
V. M. Dong, J. Am. Chem. Soc., 2009, 131, 3466; (c) L. L. Joyce
and R. A. Batey, Org. Lett., 2009, 11, 2792; (d) K. Inamoto,
C. Hasegawa, K. Hiroya and T. Doi, Org. Lett., 2008, 10, 5147;
(e) S.-I. Fukuzawa, E. Shimizu, Y. Atsuumi, M. Haga and
K. Ogata, Tetrahedron Lett., 2009, 50, 2374; (f) K. Inamoto,
Y. Arai, K. Hiroya and T. Doi, Chem. Commun., 2008, 5529;
(g) X.-L. Fang, R.-Y. Tang, P. Zhong and J.-H. Li, Synthesis,
2009, 4183; (h) S. Zhang, P. Qian, M. Zhang, M. Hu and J. Cheng,
J. Org. Chem., 2010, 75, 6732.
Scheme
2 Phenylthiolation and methylthiolation of ArI under
standard procedure.
Notes and references
1 (a) A. Gangjee, Y. Zeng, T. Talreja, J. J. McGuire, R. L. Kisliuk
and S. F. Queener, J. Med. Chem., 2007, 50, 3046; (b) G. De
Martino, M. C. Edler, G. La Regina, A. Cosuccia, M. C. Barbera,
D. Barrow, R. I. Nicholson, G. Chiosis, A. Brancale, E. Hamel,
M. Artico and R. Silvestri, J. Med. Chem., 2006, 49, 947;
(c) G. Liu, J. R. Huth, E. T. Olejniczak, F. Mendoza,
S. W. Fesik and T. W. von Geldern, J. Med. Chem., 2001,
44, 1202; (d) S. F. Nielsen, E. Ø. Nielsen, G. M. Olsen,
T. Liljefors and D. Peters, J. Med. Chem., 2000, 43, 2217;
(e) G. De Martino, G. La Regina, A. Coluccia, M. C. Edler,
M. C. Barbera, A. Brancale, E. Wilcox, E. Hamel, M. Artico and
R. Silvestri, J. Med. Chem., 2004, 47, 6120; (f) L. Liu,
J. E. Stelmach, S. R. Natarajan, M.-H. Chen, S. B. Singh,
C. D. Schwartz, C. E. Fitzgerald, S. J. O’Keefe, D. M. Zaller,
D. M. Schmatz and J. B. Doherty, Bioorg. Med. Chem. Lett., 2003,
13, 3979; (g) J. Slade, J. L. Stanton, D. Ben-David and
G. C. Mazzenga, J. Med. Chem., 1985, 28, 1517; (h) R. Garg,
A. Kurup, S. B. Mekapati and C. Hansch, Chem. Rev., 2003,
103, 703.
8 L. Chu, X. Yue and F.-L. Qing, Org. Lett., 2010, 12, 1644.
9 (a) H. Wang, L. Jiang, T. Chen and Y. Li, Eur. J. Org. Chem.,
2010, 2324; (b) N. Taniguchi and T. Onami, Synlett, 2003, 829;
(c) L. Wang, M. Wang and F. Huang, Synlett, 2005, 2007;
(d) N. Taniguchi, Synlett, 2006, 1351; (e) N. Taniguchi, J. Org.
Chem., 2007, 72, 1241; (f) P. S. Luo, M. Yu, R. Y. Tang, P. Zhong
and J.-H. Li, Tetrahedron Lett., 2009, 50, 1066; (g) N. Taniguchi
and T. Onami, J. Org. Chem., 2004, 69, 915; (h) S. Kumar and
L. Engman, J. Org. Chem., 2006, 71, 5400; (i) V. P. Reddy,
A. V. Kumar, K. Swapna and K. R. Rao, Org. Lett., 2009,
11, 951; (j) O. Baldovino-Pantaleon, S. Hernandez-Ortega and
D. Morales-Morales, Adv. Synth. Catal., 2006, 348, 236;
(k) V. Gomez-Benıtez, O. Baldovino-Pantaleon, C. Herrera-
Alvarez, R. A. Toscano and D. Morales-Morales, Tetrahedron
Lett., 2006, 47, 5059.
2 (a) A. S. Kalgutkar, K. R. Kozak, B. C. Crews and L. J. Marnett,
J. Med. Chem., 1998, 41, 4800; (b) S. A. Laufer, H.-G. Striegel and
G. K. Wagner, J. Med. Chem., 2002, 45, 4695; (c) A. Gallardo-
Godoy, A. Fierro, T. H. McLean, M. Castillo, B. K. Cassels,
M. Reyes-Parada and D. E. Nichols, J. Med. Chem., 2005,
48, 2407; (d) T. K. Pradhan and A. De J. Mortier, Tetrahedron,
2005, 61, 9007; (e) S. A. Laufer, D. R. J. Hauser, D. M. Domeyer,
K. Kinkel and A. J. Liedtke, J. Med. Chem., 2008, 51, 4122;
(f) S. A. Laufer, W. Zimmermann and K. J. Ruff, J. Med. Chem.,
2004, 47, 6311; (g) P. Koch, C. Bauerlein, H. Jank and S. Laufer,
J. Med. Chem., 2008, 51, 5630.
3 (a) K. Bahrami, M. M. Khodaei and A. Karimi, Synthesis, 2008,
2543; (b) K. Bahrami, M. M. Khodaei and M. Khedri, Chem. Lett.,
2007, 36, 1324; (c) J. M. Khurana, V. S. Sharma and A. Chacko,
Tetrahedron, 2007, 63, 966; (d) B. R. Raju, G. Devi,
Y. S. Nongpluh and A. K. Saikia, Synlett, 2005, 358;
(e) R. Sanz, J. Escribano, Y. Fernandez, R. Aguado,
M. R. Pedrosa and F. J. Arnaiz, Synthesis, 2004, 1629;
(f) D. J. Harrison, N. C. Tam, C. M. Vogels, R. F. Langler,
10 (a) V. J. Traynelis and W. L. Hergenrother, J. Org. Chem., 1964,
29, 221; (b) H. Nace and J. Monagle, J. Org. Chem., 1959, 24, 1792;
(c) W. J. Kenney, J. A. Walsh and D. A. Davenport, J. Am. Chem.
Soc., 1961, 83, 4019.
c
5306 Chem. Commun., 2011, 47, 5304–5306
This journal is The Royal Society of Chemistry 2011