X. Wu, A. E. V. Gorden
FULL PAPER
decane solution (6.0 mmol). The reaction mixture was stirred for
Supporting Information (see also the footnote on the first page of
this article): General experimental methods and H and C-NMR
spectra of the compounds produced (see Table 2).
1
13
18 h at 70 °C. After 18 h, an additional 1.0 mL of tert-butyl hydro-
peroxide decane solution (6.0 mmol) was added and the solution
was heated at reflux temperature for an additional 18 h. The reac-
tion was monitored by TLC. Once the starting material can no
longer be seen by TLC, the reaction was considered to be complete.
Pure products are obtained by purification using flash column
chromatography with a solution of hexane/ethyl acetate (10–20:1)
as eluent. The yields of final pure products were from 65–92% (see
notation in Table 2).
Acknowledgments
Funding was provided by Auburn University and the Department
of Chemistry and Biochemistry. We would like to express our ap-
preciation to Prof. C. R. Goldsmith for his helpful discussions. Lit-
1
13
erature references for H, C NMR spectra used for comparison
(National Institute of Advanced Industrial Science and Technol-
Data Section
1
Entry 1: H NMR (400 MHz, CDCl
3
): δ = 7.49 (t, 4 H), 7.62 (t, 2
H), 7.84 (d, 4 H) ppm. 13C NMR (100 MHz, CDCl
): δ = 196.8, ogy, July 2008).
3
137.6, 132.5, 130.1, 128.3 ppm.
1
Entry 2, N-Benzylidenebenzylamine: H NMR (400 MHz, CDCl
3
): [1] a) R. D. Smiley, G. G. Hammes, Chem. Rev. 2006, 106, 3080;
b) S. T. Connon, S. Blechert, Angew. Chem. Int. Ed. 2003, 42,
δ = 4.87 (s, 2 H), 7.28–7.93 (m, 10 H), 8.43 (s, 1 H) ppm. 1 C NMR
100 MHz, CDCl ): δ = 162.5, 139.0, 136.4, 134.5, 130.9, 130.6,
4.9 ppm.
Benzaldehyde: H NMR (400 MHz, CDCl
3
1
900; c) K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S.
(
3
Baran, Angew. Chem. Int. Ed. 2000, 39, 44; d) S. Caron, R. W.
Dugger, S. G. Ruggeri, J. A. Ragan, D. H. B. Ripin, Chem. Rev.
2006, 106, 2943; e) R. H. Grubbs, Angew. Chem. Int. Ed. 2006,
45, 3760; f) R. R. Schrock, Angew. Chem. Int. Ed. 2006, 45,
6
1
3
): δ = 7.50 (t, 2 H), 7.60
13
(
t, 1 H), 7.86 (d, 2 H), 10.01 (s, 1 H) ppm. C NMR (100 MHz,
3748; g) Y. Chauvin, Angew. Chem. Int. Ed. 2006, 45, 3741.
CDCl
3
): δ = 191.9, 136.0, 134.0, 129.3, 128.6 ppm.
[
[
[
2] a) P. J. Walsh, H. Li, C. A. Parrodi, Chem. Rev. 2007, 107, 2503;
b) B. Notari, Catal. Today 1993, 18, 163; c) A. Butler, M. J.
Clague, G. E. Meister, Chem. Rev. 1994, 94, 625; d) J. M. Au-
bry, S. J. Bouttemy, J. Am. Chem. Soc. 1997, 119, 5286; e) D. H.
Dickman, Chem. Rev. 1994, 94, 569.
1
Entry 3: H NMR (400 MHz, CDCl
3
): δ = 3.91 (s, 3 H), 7.43 (t, 2
H), 7.53 (t, 1 H), 8.05 (d, 2 H) ppm. 13C NMR (100 MHz, CDCl
δ = 167.1, 132.9, 130.2, 129.6, 128.4, 128.2, 126.9, 52.0 ppm.
):
3
1
Entry 4: H NMR (250 MHz, CDCl
3
): δ = 2.71 (s, 3 H), 8.15 (d, 2
): δ = 196.3,
3] a) G. Dyker, Angew. Chem. Int. Ed. 1999, 38, 1698; b) T. Naota,
H. Takaya, S.-I. Murahashi, Chem. Rev. 1998, 98, 2599; c) V.
Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731; d)
H. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000,
287, 1995; e) A. S. Goldman, Nature 1993, 366, 514.
H), 8.35 (d, 2 H) ppm. 13C NMR (62.5 MHz, CDCl
3
1
41.4, 129.3, 123.9, 27.0 ppm.
1
Entry 5: H NMR (400 MHz, CDCl
3
): δ = 1.43 (t, 3 H), 4.60 (q, 2
H), 7.53 (t, 2 H), 7.67 (t, 1 H), 8.01 (d, 2 H) ppm. 1 C NMR
3
4] a) A. Erkkila, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107,
(
100 MHz, CDCl ): δ = 186.5, 163.9, 134.9, 132.4, 130.0, 128.9,
2.4, 14.1 ppm.
3
5
416; b) D. Darensbourg, Chem. Rev. 2007, 107, 2388; c) N. E.
6
Borisova, M. D. Reshetova, Y. A. Ustynyuk, Chem. Rev. 2007,
107, 49; d) S. E. Denmark, E. N. Jacobsen, Acc. Chem. Res.
1
Entry 6: H NMR (400 MHz, CDCl
3
): δ = 1.02 (t, 3 H), 1.97 (m,
2000, 33, 324; e) S. Dey, D. R. Powell, C. Hu, D. B. Berkowitz,
2
H), 2.96 (t, 2 H), 7.46 (t, 2 H), 7.53 (t, 1 H), 7.96 (d, 2 H) ppm.
C NMR (100 MHz, CDCl ): δ = 200.4, 137.1, 132.9, 128.4, 128.2,
3
28.0, 40.5, 27.2, 13.9 ppm.
13
Angew. Chem. Int. Ed. 2007, 46, 7010; f) A. Pui, J.-P. Mahy,
Polyhedron 2007, 26, 3143; g) Z. Lue, M. Yuan, F. Pan, S. Gao,
D. Zhang, D. Zhu, Inorg. Chem. 2006, 45, 3538.
1
1
Entry 7: H NMR (400 MHz, CDCl
3
): δ = 7.50 (t, 4 H), 7.62 (t, 2
): δ = 196.8,
[5] S. Velusamy, T. Punniyamurthy, Tetrahedron Lett. 2003, 44,
H), 7.85 (d, 4 H) ppm. 13C NMR (100 MHz, CDCl
8955.
3
[
6] a) H. B. Henbest, B. Nicholls, J. Chem. Soc. 1959, 221; b) S.
Harrison, Chem. Commun. (London) 1966, 752; c) A. J. Cat-
ino, R. E. Forslund, M. P. Doyle, J. Am. Chem. Soc. 2004, 126,
13622; d) H. M. C. Ferraz Jr., L. S. Longo, Org. Lett. 2003, 5,
1337; e) R. Breslow, P. C. Scholl, J. Am. Chem. Soc. 1971, 93,
1
37.6, 132.4, 130.1, 128.3 ppm.
1
Entry 8: H NMR (400 MHz, CDCl
3
): δ = 2.57 (s, 3 H), 7.49 (t, 2
H), 7.60 (t, 1 H), 7.94 (d, 2 H) ppm. 13C NMR (100 MHz, CDCl
):
3
δ = 198.4, 137.3, 133.6, 129.1, 128.6, 27.2 ppm.
2
3
1
331; f) J. Q. Yu, E. J. Coery, J. Am. Chem. Soc. 2003, 125,
232; g) S. Tsunoi, I. Ryu, N. Sonoda, J. Am. Chem. Soc. 1994,
16, 5473.
1
Entry 9: H NMR (400 MHz CDCl
3
): δ = 7.50 (t, 2 H), 7.60 (t, 1
H), 7.86 (d, 2 H), 10.01 (s, 1 H) ppm. 13C NMR (100 MHz,
CDCl
3
): δ = 191.9, 136.0, 134.0, 129.3, 128.6 ppm.
[
7] a) A. Krief, L. Hevesi, Organoselenium Chemistry I, Springer,
NY, 1998, 115; b) E. S. Krongauz, Russ. Chem. Rev. 1977, 46,
59; c) N. Rabjohn, Org. React. 1976, 24, 261; d) E. J. Coery,
J. P. Schaefer, J. Am. Chem. Soc. 1960, 82, 918; e) K. B.
Sharpless, K. M. Gordon, J. Am. Chem. Soc. 1976, 98, 300.
1
Entry 10: H NMR (400 MHz, [D
dd, 2 H), 8.13 (dd, 2 H) ppm. C NMR (100 MHz, [D ]DMSO):
6
δ = 185.1, 138.7, 134.0, 131.9, 126.5 ppm.
6
]DMSO): δ = 7.02 (s, 2 H), 7.80
13
(
1
Entry 11: H NMR (250 MHz, CDCl
3
): δ = 2.71 (s, 3 H), 7.56 (m, [8] a) J. H. Markgraf, B. Y. Choi, Synth. Commun. 1999, 29, 2405;
b) J. H. Markgraf, C. A. Stickney, J. Heterocycl. Chem. 2000,
H), 7.62 (m, 4 H), 8.05 (s, 1 H) ppm. 1 C NMR (62.5 MHz,
3
2
3
6
7, 109; c) S. Negele, K. Wieser, T. Severin, J. Org. Chem. 1998,
3, 1138; d) H. X. Wei, R. L. Jasoni, H. Shao, J. Hu, P. W. Pare,
3
CDCl ): δ = 198.1, 135.6, 134.4, 132.5, 130.2, 129.6, 128.5, 128.4,
27.8, 126.8, 123.9 ppm.
1
Tetrahedron 2004, 60, 11829.
1
Entry 17: H NMR (400 MHz, CDCl
3
): δ = 7.57–7.96 (m, 5 H), [9] a) H. H. Wasserman, J. L. Ives, J. Org. Chem. 1978, 43, 3238;
8
=
.54 (d, 1 H), 9.27 (s, 2 H) ppm. 13C NMR (100 MHz, CDCl
3
): δ
b) H. H. Wasserman, J. L. Ives, J. Org. Chem. 1985, 50, 3573;
c) D. V. Rao, F. A. Stuber, H. Ulrich, J. Org. Chem. 1979, 44,
152.5, 142.9, 135.8, 130.4, 127.6, 127.3, 126.5, 120.5 ppm.
4
56; d) P. Li, W. M. Fong, L. C. F. Chao, S. H. C. Fung, I. D.
1
Entry 18: H NMR (400 MHz, CDCl
H), 7.63 (t, 1 H), 7.73 (d, 1 H), 8.06 (m, 2 H), 8.60 (m, 1 H) ppm.
C NMR (100 MHz, CDCl
27.8, 126.5, 121.0 ppm.
3
): δ = 7.29 (m, 1 H), 7.47 (t,
Williams, J. Org. Chem. 2001, 66, 4087.
1
[
10] a) J. C. Lee, H. J. Park, J. Y. Park, Tetrahedron Lett. 2002, 43,
5661; b) Z. Li, C. G. Xiu, C. Z. Xu, Tetrahedron Lett. 2003, 44,
9229; c) N. K. Sharma, K. N. Ganesh, Tetrahedron Lett. 2004,
13
3
): δ = 150.3, 148.2, 136.0, 129.4, 128.2,
1
508
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