PAPER
Copper(I) Iodide Catalyzed Diaryl Selenide Synthesis
2301
GC-MS (EI+): m/z = 233.
A.D. and C.K. thank CSIR, New Delhi, and D.J.C.P. thanks UGC,
New Delhi for a fellowship.
1-[4-(Phenylselanyl)phenyl]ethanone (15)7c
Orange solid; mp 55–57 °C (Lit.17 57 °C); Rf = 0.53 (EtOAc–hex-
anes, 1:19).
References
IR (neat): 3063, 2990, 1675, 821, 737, 690 cm–1.
1H NMR (400 MHz, CDCl3): d = 2.55 (s, 3 H), 7.33–7.45 (m, 5 H),
7.57–7.63 (m, 2 H), 7.76–7.84 (m, 2 H).
13C NMR (100 MHz, CDCl3): d = 26.6, 128.6, 128.8, 129.1, 129.9,
130.5, 135.2, 135.3, 140.4, 197.5.
HRMS: m/z [M + H]+ calcd for C14H13OSe: 277.0132; found:
277.0139.
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(2-Bromophenyl)(phenyl)selane (16)6a
Slightly brown oil; Rf = 0.63 (hexanes).
IR (neat): 3053, 2956, 2922, 2850, 735, 688, 478 cm–1.
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Schinazi, R. F. J. Med. Chem. 1993, 36, 4250.
1H NMR (400 MHz, CDCl3): d = 6.87–7.20 (m, 3 H), 7.35–7.62 (m,
4 H), 7.63–7.82 (m, 2 H).
13C NMR (100 MHz, CDCl3): d = 123.6, 127.4, 127.9, 128.6, 129.0,
1129.9, 130.6, 132.8, 136.3, 136.5.
GC-MS (EI+): m/z = 312.
(3,5-Dimethylphenyl)(phenyl)selane (17)9g
Colorless oil; Rf = 0.66 (hexanes).
IR (neat): 2921, 2852, 1573, 733, 684 cm–1.
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1H NMR (400 MHz, CDCl3): d = 2.17 (s, 6 H), 6.81 (s, 1 H), 7.04
(s, 2 H), 7.12–7.21 (m, 3 H), 7.31–7.39 (m, 2 H).
13C NMR (100 MHz, CDCl3): d = 127.1, 129.3, 129.5, 130.4, 131.1,
131.7, 132.6, 139.1.
GC-MS (EI+): m/z = 261.
2-(Phenylselanyl)pyridine (18)9a
Colorless oil; Rf = 0.54 (EtOAc–hexanes, 1:9).
IR (neat): 3045, 2922, 2852, 1570, 1414, 1083, 741 cm–1.
1H NMR (400 MHz, CDCl3): d = 6.97–7.05 (m, 2 H), 7.33–7.46 (m,
4 H), 7.64–7.76 (m, 2 H), 8.43 (d, J = 4.4 Hz, 1 H).
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Okada, M.; Kuroki, T.; Watanabe, T.; Nishiyama, Y.;
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13C NMR (100 MHz, CDCl3): d = 120.5, 124.3, 128.0, 129.0, 129.8,
136.3, 136.8, 150.0, 158.9.
GC-MS (EI+): m/z = 234.
4-(Phenylselanyl)benzonitrile (19)6a
Colorless oil; Rf = 0.65 (EtOAc–hexanes, 1:19).
IR (neat): 3071, 2226, 823, 737, 644 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.30–7.49 (m, 7 H), 7.58–7.65 (m,
2 H).
13C NMR (100 MHz, CDCl3): d = 109.6, 118.9, 127.5, 129.2, 130.0,
130.3, 132.5, 135.7, 141.1.
GC-MS (EI+): m/z = 258.
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Supporting Information for this article is available online at
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951.
Acknowledgment
We thank DST, New Delhi for financial support (Project No.: SR/
S1/OC-06/2008) and for funding towards the 400 MHz NMR spec-
trometer at the Department of Chemistry, IIT Madras under the IR-
PHA scheme, and the ESI-MS facility under the FIST programme.
Synthesis 2011, No. 14, 2297–2302 © Thieme Stuttgart · New York