The Journal of Organic Chemistry
Note
Scheme 1. Observed Reaction Intermediate 4a in the Reaction of 1a with 2a
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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This work was supported by the MEXT-Supported Program for
the Strategic Research Foundation at Private Universities
(2010-2014), ALCA from Japan Science and Technology
Agency (JST), and the Kansai University Research Grants:
Grant-in Aid for Encouragement of Scientists, 2012.
REFERENCES
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(1) (a) Sundbelg, R. J. In Kirk-Othmer Encyclopedia of Chemical
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Figure 2. Plausible reaction pathway.
133.6 (C), 132.0 (C), 129.4 (CH), 128.9 (CH), 127.9 (CH), 127.6
(CH), 127.5 (CH), 127.5 (CH), 127.3 (CH), 126.8 (C), 126.6 (CH),
125.9 (CH), 125.8 (CH), 125.2 (CH), 121.6 (CH), 40.9 (CH2), 36.0
(CH2); IR (neat, cm−1) 2916, 1597, 1501, 1425, 1126, 858, 829, 746;
GC−MS (EI) m/z (relative intensity) 283 (88) [M]+, 282 (100), 156
(35), 155 (4), 142 (9), 141 (44), 128 (17), 127 (4). Anal. Calcd for
C21H17N: C, 89.01; H, 6.05; N, 4.94. Found: C, 89.01; H, 5.97; N,
4.93.
Compound 3h. Yield 36% (96 mg), yellow solid, mp 56−57 °C;
1H NMR δ 8.07−7.12 (m, 10H), 3.26−3.22 (m, 2H), 3.14−3.10 (m,
2H); 13C NMR δ 161.2 (C), 147.9 (C), 139.9 (C), 136.2 (CH), 131.6
(C), 129.8 (CH), 129.4 (CH), 128.8 (CH), 128.4 (CH), 127.5 (CH),
126.7 (C), 125.8 (CH), 121.4 (CH), 40.6 (CH2), 35.0 (CH2); IR
(neat, cm−1) 3057, 2924, 1600, 1501, 1427, 1090, 1013, 827, 762;
GC−MS (EI) m/z (relative intensity) 267 (89) [M]+, 266 (100), 232
(7), 156 (70), 142 (4), 128 (22), 125 (19), 91(1), 77(9); HRMS (EI-
TOF) m/z calcd for C17H14NCl [M]+ 267.0815, found 267.0820.
́
Rivas, K.; Yokoyama, K.; Hoeney, C. P.; Pendyala, P. R.; Floyd, D.;
Lombardo, L. J.; Williams, D. K.; Hamilton, A.; Sebti, S.; Windsor, W.
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21, 1549.
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Organomet. Chem. 2011, 34, 77. (b) Zhang, J.; Leitus, G.; Ben-David,
Y.; Milstein, D. J. Am. Chem. Soc. 2005, 127, 10840. (c) Hanasaka, F.;
Fujita, K.; Yamaguchi, R. Organometallics 2004, 23, 1490. (d) Hamid,
M. H. S. A.; Slatford, P. A; Williams, J. M. J. Adv. Synth. Catal. 2007,
349, 1555. (e) Bower, J. F.; Kim, I. S.; Patman, R. L.; Krische, M. J.
Angew. Chem., Int. Ed. 2009, 48, 34. (f) Guillena, G.; Ramon, D. J.;
Yus, M. Chem. Rev. 2010, 110, 1611. (g) Debereiner, G. E.; Crabtree,
R. H. Chem. Rev. 2010, 110, 681. (h) Takeuchi, R.; Kezuka, S. Synthesis
2006, 3349.
1
Compound 3l. Yield 78% (199 mg), yellow liquid; H NMR δ
7.98−7.18 (m, 6H), 2.90−2.86 (m, 2H), 1.70−1.67 (m, 2H), 1.33−
1.21 (m, 9H), 0.83−0.80 (t, J = 7.2 Hz 3H), 0.83−0.79 (t, J = 7.2, Hz
3H); 13C NMR δ 163.47 (C), 147.9 (C), 136.1 (CH), 129.2 (CH),
128.8 (CH), 127.4 (CH), 126.7 (C), 125.6 (C), 121.3 (CH), 38.9
(CH), 36.8 (CH2), 33.5 (CH2), 32.7 (CH2), 28.9 (CH2), 25.7 (CH2),
23.1 (CH2), 14.1 (CH3), 10.8 (CH3); IR (neat, cm−1) 2956, 2926,
2859, 1601, 1504, 1458, 1425, 826, 752; GC−MS (EI) m/z (relative
intensity) 255 (1) [M]+, 226 (6), 198 (5), 184 (2), 170 (1), 156 (39),
143 (100), 142 (4), 128 (6), 57 (2), 43 (2), 29 (4); HRMS (EI-TOF)
m/z calcd for C18H25N [M]+ 255.1987, found 255.1993.
(5) For selected examples, see: (a) Cho, C. S.; Kim, B. T.; Kim, T.-J.;
Shim, S. C. J. Org. Chem. 2001, 66, 9020. (b) Ndou, A. S.; Plint, N.;
Coville, N. J. Appl. Catal. A: Gen. 2003, 251, 337. (c) Cho, C. S.; Kim,
B. T.; Kim, H.-S.; Kim, T.-J.; Shim, S. C. Organometallics 2003, 22,
́
3608. (d) Martínez, R.; Ramon, D. J.; Yus, M. Tetrahedron 2006, 62,
8982. (e) Fujita, K.; Asai, C.; Yamaguchi, T.; Hanasaka, F.; Yamaguchi,
R. Org. Lett. 2005, 7, 4017. (f) Onodera, G.; Nishibayashi, Y.; Uemura,
S. Angew. Chem., Int. Ed. 2006, 45, 3819. (g) Guillena, G.; Ramon, D.
J.; Yus, M. Angew. Chem., Int. Ed. 2007, 46, 2358. (h) Nixon, T. D.;
Whittlesey, M. K.; Williams, J. M. J. Dalton Trans. 2009, 753 and
references therein.
ASSOCIATED CONTENT
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(6) (a) Taniguchi, K.; Nakagawa, H.; Hirabayashi, T.; Sakaguchi, S.;
Ishii, Y. J. Am. Chem. Soc. 2004, 126, 72. (b) Maeda, K.; Obora, Y.;
Sakaguchi, S.; Ishii, Y. Bull. Chem. Soc. Jpn. 2008, 81, 689. (c) Iuchi, Y.;
Obora, Y.; Ishii, Y. J. Am. Chem. Soc. 2010, 132, 2536. (d) Morita, M.;
Obora, Y.; Ishii, Y. Chem. Commun. 2007, 2850. (e) Obora, Y.; Anno,
Y.; Okamoto, R.; Matsu-ura, T.; Ishii, Y. Angew. Chem., lnd. Ed. 2011,
50, 8618. (f) Matsu-ura, T.; Sakaguchi, S.; Obora, Y.; Ishii, Y. J. Org.
Chem. 2006, 71, 8306.
S
* Supporting Information
1H, and 13C NMR spectra for products. This material is
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dx.doi.org/10.1021/jo3019347 | J. Org. Chem. XXXX, XXX, XXX−XXX