7650
Y. Goriya, C.V. Ramana / Tetrahedron 66 (2010) 7642e7650
7.96e8.02 (m, 2H), 8.53e8.57 (m, 1H) ppm; 13C NMR (CDCl3,
50 MHz): 122.0 (d), 122.7 (d), 126.4 (d), 126.5 (d), 126.7 (d), 127.5
(d), 128.7 (d), 129.9 (d), 136.6 (d), 137.0 (d), 148.3 (s), 150.2 (d), 156.3
(s), 157.6 (s) ppm; MALDIeMS (m/z): 239.0616 [Mþ1]þ. Anal. Calcd
for C14H10N2S: C, 70.56; H, 4.23; N, 11.76. Found: C, 70.61; H, 4.16; N,
11.68.
Lang, F. R.; Zewge, D.; Houpis, I. N.; Volante, R. P. Tetrahedron Lett. 2001, 42,
3251e3254.
8. Selected reviews on thioether synthesis: (a) Ley, S. V.; Thomas, A. W. Angew.
Chem., Int. Ed. 2003, 42, 5400e5449; (b) Kondo, T.; Mitsudo, T.-A. Chem. Rev.
2000, 100, 3205e3220.
d
9. For reduction of azides see: (a) Brase, S.; Gil, C.; Knepper, K.; Zimmermann, V.
Angew. Chem., Int. Ed. 2005, 44, 5188e5240; (b) Scriven, E. F. V.; Turnbull, K.
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74, 2203e2206; (f) Ayesa, S.; Samuelsson, B.; Classon, B. Synlett 2008, 97e99;
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D’Anna, F.; Marullo, S.; Noto, R. J. Org. Chem. 2010, 75, 767e771; (b) D’Anna, F.;
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J.; Liu, A. X.; Liu, L.; Guo, Q. X. Tetrahedron Lett. 2007, 48, 3525e3529; (d) An-
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4.3.24. 2-[n-Dodecylmercapto]-quinoline (7jd)22g. Colorless oil; Rf
(100% pet. ether) 0.3; IR (CHCl3)
n
: 1614, 1594, 1497, 1465, 1376,
;
1294, 1137, 1088, 814, 779, 747 cmꢂ1
1H NMR (CDCl3, 200 MHz):
d
0.88 (t, J¼6.5 Hz, 3H), 1.25 (br s, 16H), 1.41e1.51 (m, 2H), 1.70e1.81
(m, 2H), 3.33 (t, J¼7.3 Hz, 2H), 7.18 (d, J¼8.7 Hz, 1H), 7.38 (ddd,
J¼1.2, 7.1, 8.1 Hz, 1H), 7.57e7.69 (m, 2H), 7.82 (d, J¼8.7 Hz, 1H),
7.90e7.94 (m, 1H) ppm; 13C NMR (CDCl3, 50 MHz):
d 14.1 (q), 22.6
(t), 29.0 (t), 29.2 (t), 29.3 (t, 2C), 29.5 (t), 29.6 (t, 2C), 29.6 (t), 29.7 (t),
31.9 (t), 121.0 (d), 125.0 (d), 125.8 (s), 127.5 (d), 128.0 (d), 129.4 (d),
135.0 (d), 148.3 (s), 159.6 (s) ppm; MALDIeMS (m/z): 330.2256
[Mþ1]þ. Anal. Calcd for C21H31NS: C, 76.54; H, 9.48; N, 4.25. Found:
C, 76.61; H, 9.43; N, 4.17.
€
Madsen, U.; Bjorkling, F.; Liang, X. Synlett 2005, 2209e2213; (f) Feldman, A. K.;
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Biomol. Chem. 2007, 5, 1695e1701.
12. During this work in progress, Molander and co-workers reported the formation
of aniline derivatives during the azidation of aryl tetrafluorborates and is
substrate specificdsee: Cho, Y. A.; Kim, D. S.; Ahn, H. R.; Canturk, B.; Molander,
G. A.; Ham, J. Org. Lett. 2009, 11, 4330e4333.
13. During this manuscript in preparation, Qiao and Sajiki groups reported a simi-
lar copper catalyzed direction amination of aryl halide using azide as the am-
monia source. (a) Monguchi, Y.; Maejima, T.; Mori, S.; Maegawa, T.; Sajiki, H.
Chem.dEur. J. 2010, 16, 7372e7375; (b) Ref. 9c.
14. (a) Lee, G.-Y. J. Korean Chem. Soc. 2009, 53, 257e265; (b) Bartoli, G.; Di Antonio,
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2008, 73, 1919e1924; (c) Antsyshkina, A. S.; Sadikov, G. G.; Sergienko, V. S.;
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4.3.25. 4-Methoxyphenyl phenyl sulfide (7ka). Colorless oil; Rf
(100% pet. ether) 0.3; 1H NMR (CDCl3, 200 MHz):
d
3.82 (s, 3H),
6.86e6.93 (m, 2H), 7.09e7.28 (m, 5H), 7.38e7.46 (m, 2H) ppm; 13C
NMR (CDCl3, 50 MHz): 55.3 (q), 115.0 (d, 2C), 124.2 (s), 125.7 (d),
d
128.2 (d, 2C), 128.9 (d, 2C), 135.4 (d, 2C), 138.6 (s), 159.8 (s) ppm.
Acknowledgements
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We thank the Ministry of Science and Technology for funding
through the Department of Science and Technology under the
Green Chemistry Program (NO. SR/S5/GC-20/2007).
Supplementary data
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Supporting information available: NMR spectra of representa-
tive compounds. Supplementary data associated with this article
These data include MOL files and InChIKeys of the most important
compounds described in this article.
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