I
L. Blank et al.
Paper
Synthesis
3-Nitrothioanisole (5m)
Paone, A.; Ho, G. J.; Pipik, B.; Helmy, R.; McNamara, J. M.; Shi, Y.
J.; Williams, J. M.; Macdonald, D.; Deschenes, D.; Gallant, M.;
Mastracchio, A.; Roy, B.; Scheigetz, J. Org. Process Res. Dev. 2006,
10, 36. (e) Jarvest, R. L.; Berge, J. M.; Brown, M. J.; Brown, P.;
Elder, J. S.; Forrest, A. K.; Houge-Frydrych, C. S. V.; O’Hanlon, P.
J.; McNair, D. J.; Rittenhouse, S.; Sheppard, R. J. Bioorg. Med.
Chem. Lett. 2003, 13, 665.
Reaction of 1s (33.8 mg, 0.20 mmol) and 4a (37.7 mg, 0.40 mmol, 2.00
equiv) in MeCN (2.00 mL, 0.1 M) gave 5m (18.2 mg, 10.8·10–2 mmol,
54%) after purification by column chromatography on silica gel with a
mixture of pentane/Et2O as a yellow solid.
1H NMR (600 MHz, CDCl3): δ = 8.05 (t, J = 1.9 Hz, 1 H), 7.96 (ddd, J =
5.8, 1.9, 0.7 Hz, 1 H), 7.55–7.51 (m, 1 H), 7.43 (t, J = 8.0 Hz, 1 H), 2.56
(s, 3 H).
(5) (a) Waldrop, F. N.; Robertson, R. H.; Vourlekis, A. Compr. Psychi-
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Murphy, B. L.; Fischer, P. A. J. Org. Chem. 1990, 55, 5291.
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Sci. 1997, 50, 83. (e) Lu, W. Y.; Chen, P.; Lin, G. Q. Tetrahedron
2008, 64, 7822. (f) Van Soolingen, D.; Hernandez-Pando, R.;
Orozco, H.; Aguilar, D.; Magis-Escurra, C.; Amaral, L.; van Ingen,
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D. H.; Litomska, A.; Hertweck, C. Chem. Rev. 2017, 117, 5521.
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The NMR data were in accordance with the literature.21
Ethyl Phenyl Sulfide (5n)
Reaction of 1a (36.8 mg, 0.20 mmol) and diethyl disulfide (4b; 49 mg,
0.40 mmol, 2.00 equiv) in MeCN (2.00 mL, 0.1 M) gave 5n (13.9 mg,
10.1·10–2 mmol, 50%) after purification by column chromatography
on silica gel with pentane as a colourless oil.
1H NMR (400 MHz, CDCl3): δ = 7.40–7.25 (m, 4 H), 7.22–7.11 (m, 1 H),
2.95 (q, J = 7.4 Hz, 2 H), 1.32 (dd, J = 9.2, 5.5 Hz, 3 H).
The NMR data were in accordance with the literature.25
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183. (b) Ban, H. S.; Nakamura, H. Chem. Rec. 2015, 15, 616.
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2300. (c) Baron, O.; Knochel, P. Angew. Chem. Int. Ed. 2005, 44,
3133.
Diphenyl Sulfide (5o)
Reaction of 1a (36.8 mg, 0.20 mmol) and diphenyl disulfide (4c; 87.3
mg, 0.40 mmol, 2.00 equiv) in MeCN (2.00 mL, 0.1 M) gave 5o
(17.2 mg, 9.23·10–2 mmol, 46%) after purification by column chroma-
tography on silica gel with pentane as a colourless oil.
(9) (a) Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60,
7508. (b) Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F.
Science 2000, 287, 1995. (c) Shimada, S.; Batsanov, A. S.;
Howard, J. A. K.; Marder, T. B. Angew. Chem. Int. Ed. 2001, 40,
2168. (d) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.;
Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390.
(e) Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2003, 680, 3.
(f) Adams, C. J.; Baber, R. A.; Batsanov, A. S.; Bramham, G.;
Charmant, J. P. H.; Haddow, M. F.; Howard, J. A. K.; Lam, W. H.;
Lin, Z.; Marder, T. B.; Norman, N. C.; Orpen, A. G. Dalton Trans.
2006, 11, 1370. (g) Zhu, W.; Ma, D. Org. Lett. 2006, 8, 261.
(h) Billingsley, K. L.; Barder, T. E.; Buchwald, S. L. Angew. Chem.
Int. Ed. 2007, 46, 5359. (i) Rosen, B. M.; Huang, C.; Percec, V. Org.
Lett. 2008, 10, 2597. (j) Kleeberg, C.; Dang, L.; Lin, Z.; Marder, T.
B. Angew. Chem. Int. Ed. 2009, 48, 5350. (k) Wilson, D. A.;
Wilson, C. J.; Moldoveanu, C.; Resmerita, A. M.; Corcoran, P.;
Hoang, L. M.; Rosen, B. M.; Percec, V. J. Am. Chem. Soc. 2010, 132,
1800. (l) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J.
M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890. (m) Moldoveanu, C.;
Wilson, D. A.; Wilson, C. J.; Leowanawat, P.; Resmerita, A.-M.;
Liu, C.; Rosen, B. M.; Percec, V. J. Org. Chem. 2010, 75, 5438.
(n) Chow, W. K.; So, C. M.; Lau, C. P.; Kwong, F. Y. Chem. Eur. J.
2011, 17, 6913. (o) Kawamorita, S.; Ohmiya, H.; Iwai, T.;
Sawamura, M. Angew. Chem. Int. Ed. 2011, 50, 8363.
(p) Yamamoto, T.; Morita, T.; Takagi, J.; Yamakawa, T. Org. Lett.
2011, 13, 5766. (q) Huang, K.; Yu, D.-G.; Zheng, S.-F.; Wu, Z.-H.;
Shi, Z.-J. Chem. Eur. J. 2011, 17, 786. (r) Molander, G. A.; Trice, S.
L. J.; Kennedy, S. M. J. Org. Chem. 2012, 77, 8678. (s) Chow, W.
K.; Yuen, O. Y.; Choy, P. Y.; So, C. M.; Lau, C. P.; Wong, W. T.;
Kwong, F. Y. RSC Adv. 2013, 3, 12518. (t) Molander, G. A.;
Cavalcanti, L. N.; Garcia-Garcia, C. J. Org. Chem. 2013, 78, 6427.
(u) Marciasini, L. D.; Richy, N.; Vaultier, M.; Pucheault, M. Adv.
Synth. Catal. 2013, 355, 1083. (v) Bose, S. K.; Marder, T. B. Org.
Lett. 2014, 16, 4562. (w) Zarate, C.; Manzano, R.; Martin, R.
J. Am. Chem. Soc. 2015, 137, 6754. (x) Frank, R.; Howell, J.;
Campos, J.; Tirfoin, R.; Phillips, N.; Zahn, S.; Mingos, D. M. P.;
1H NMR (400 MHz, CDCl3): δ = 7.70–6.70 (m, 10 H).
The NMR data were in accordance with the literature.19
Supporting Information
Supporting information for this article is available online at
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