D.C. Samblanet, J.A.R. Schmidt / Journal of Organometallic Chemistry 720 (2012) 7e18
17
3J ¼ 7.2 Hz, 3H), 1.21 (m, 10H), 2.76 (d, 3J ¼ 7.2 Hz, 1H), 3.04 (m, 1H),
6.41 (dd, 3J ¼ 8.0 Hz, 4J ¼ 2.4 Hz,1H), 6.77 (dd, 3J ¼ 8.0 Hz, 3J ¼ 4.8 Hz,
1H), 8.08 (d, 4J ¼ 2.4 Hz, 1H), 8.17 (d, 3J ¼ 4.8 Hz, 1H); 13C{1H} NMR
[9] C.C.C. Johansson Seechurn, M.O. Kitching, T.J. Colacot, V. Snieckus, Angew.
Chem. Int. Ed. 51 (2012) 5062e5085.
[10] T.E. Muller, K.C. Hultzsch, M. Yus, F. Foubelo, M. Tada, Chem. Rev. 108 (2008)
3795e3892.
[11] F. Pohlki, S. Doye, Chem. Soc. Rev. 32 (2003) 104e114.
[12] U. Dzhemilev, G. Tolstikov, R. Khusnutdinov, Russ. J. Org. Chem. 45 (2009)
957e987.
[13] S. Hong, T.J. Marks, Acc. Chem. Res. 37 (2004) 673e686.
[14] J.F. Hartwig, Pure Appl. Chem. 76 (2004) 507e516.
[15] J.F. Hartwig, Acc. Chem. Res. 41 (2008) 1534e1544.
[16] D.S. Surry, S.L. Buchwald, Chem. Sci. 2 (2011) 27e50.
[17] C.M. So, F.Y. Kwong, Chem. Soc. Rev. 40 (2011) 4963e4972.
[18] D.S. Surry, S.L. Buchwald, Angew. Chem. Int. Ed. 47 (2008) 6338e6361.
[19] A.S. Guram, R.A. Rennels, S.L. Buchwald, Angew. Chem. Int. Ed. 34 (1995)
1348e1350.
[20] M. Kosugi, M. Kameyama, T. Migita, Chem. Lett. 12 (1983) 927e928.
[21] N.V. Kondratenko, A.A. Kolomeitsev, V.O. Mogilevskaya, N.M. Varlamova,
L.M. Yagupolskii, Zh. Org. Khim. 22 (1986) 1721e1729.
[22] J. Louie, J.F. Hartwig, Tetrahedron Lett. 36 (1995) 3609e3612.
[23] X.W. Hao, J. Yuan, G.A. Yu, M.Q. Qiu, N.F. She, Y. Sun, C. Zhao, S.L. Mao, J. Yin,
S.H. Liu, J. Organomet. Chem. 706 (2012) 99e105.
(C6D6)
d 14.31, 20.37, 22.99, 26.28, 29.62, 32.14, 37.02, 47.99, 117.82,
123.65, 137.30, 138.80, 143.76; HRMScalc: 207.1861 for C13H23N2
[M þ H]þ; HRMSmeas: 207.1853.
4.2.2.9. N-(2-pyridyl)-2-methylindoline (Table 4, entry 12a).
1H NMR (C6D6)
d
1.36 (d, 3J ¼ 6.4 Hz, 3H), 2.71 (dd, 2J ¼ 15.6 Hz,
3J ¼ 2.4 Hz, 1H), 3.44 (dd, 2J ¼ 15.6 Hz, 3J ¼ 9.2 Hz, 1H), 4.67 (m, 1H),
6.76 (dd, 3J ¼ 7.6 Hz, 3J ¼ 4.8 Hz, 1H), 6.90 (t, 3J ¼ 7.6 Hz, 1H), 6.93 (d,
3J ¼ 7.6 Hz, 1H), 7.20 (t, 3J ¼ 7.6 Hz, 1H), 7.22 (d, 3J ¼ 7.6 Hz, 1H), 7.56
(td, 3J ¼ 7.6 Hz, 4J ¼ 2.0 Hz, 1H), 8.03 (d, 3J ¼ 7.6 Hz, 1H), 8.35 (dd,
3J ¼ 4.8 Hz, 4J ¼ 2.0 Hz, 1H); 13C{1H} NMR (C6D6)
d 19.93, 36.42,
56.56, 109.11, 113.93, 114.41, 120.71, 125.11, 127.25, 130.56, 137.28,
143.95, 148.22, 154.97; HRMScalc: 211.1235 for C14H15N2 [M þ H]þ;
HRMSmeas: 211.1240.
[24] S. Meiries, A. Chartoire, A.M.Z. Slawin, S.P. Nolan, Organometallics 31 (2012)
3402e3409.
[25] L. Zhu, Y.M. Ye, L.X. Shao, Tetrahedron 68 (2012) 2414e2420.
[26] B.J. Tardiff, R. McDonald, M.J. Ferguson, M. Stradiotto, J. Org. Chem. 77 (2012)
1056e1071.
[27] T.A. Moss, M.S. Addie, T. Nowak, M.J. Waring, Synlett 2 (2012) 285e289.
[28] D.H. Lee, A. Taher, S. Hossain, M.J. Jin, Org. Lett. 13 (2011) 5540e5543.
[29] A. Chartoire, M. Lesieur, A.M.Z. Slawin, S.P. Nolan, C.S.J. Cazin, Organometallics
30 (2011) 4432e4436.
[30] T. Tu, W.W. Fang, J. Jiang, Chem. Commun. 47 (2011) 12358e12360.
[31] D. Maiti, B.P. Fors, J.L. Henderson, Y. Nakamura, S.L. Buchwald, Chem. Sci. 2
(2011) 57e68.
[32] B.P. Fors, S.L. Buchwald, J. Am. Chem. Soc. 132 (2010) 15914e15917.
[33] R.J. Lundgren, M. Stradiotto, Chem. Eur. J. 18 (2012) 9758e9769.
[34] J. Tsuji, Palladium Reagents and Catalysts, John Wiley & Sons, Chichester, West
Sussex, England, 2004.
[35] A.R. Shaffer, J.A.R. Schmidt, Chem. Eur. J. 15 (2009) 2662e2673.
[36] J.F. Beck, J.A.R. Schmidt, RSC Adv. 2 (2012) 128e131.
[37] G. Kuchenbeiser, A.R. Shaffer, N.C. Zingales, J.F. Beck, J.A.R. Schmidt,
J. Organomet. Chem. 696 (2011) 179e187.
[38] A.R. Shaffer, J.A.R. Schmidt, Organometallics 27 (2008) 1259e1266.
[39] A.R. Shaffer, J.A.R. Schmidt, Organometallics 28 (2009) 2494e2504.
[40] J.F. Hartwig, Inorg. Chem. 46 (2007) 1936e1947.
[41] L. Ackermann, W. Song, R. Sandmann, J. Organomet. Chem. 696(2011) 195e201.
[42] A.J.A. Watson, A.C. Maxwell, J.M.J. Williams, J. Org. Chem. 76 (2011) 2328e2331.
[43] G. Manolikakes, A. Gavryushin, P. Knochel, J. Org. Chem. 73 (2008) 1429e
1434.
4.2.2.10. N-(3-pyridyl)tetrahydroquinoline (Table 4, entry 13b).
1H NMR (CDCl3)
d
2.05 (m, 2H), 2.85 (t, 3J ¼ 6.4 Hz, 2H), 3.64 (t,
3J ¼ 6.4 Hz, 2H), 6.79 (t, 3J ¼ 4.8 Hz,1H), 6.80 (d, 3J ¼ 7.6 Hz,1H), 6.97
(t, 3J ¼ 7.6 Hz, 1H), 7.08 (d, 3J ¼ 7.6 Hz, 1H), 7.25 (t, 3J ¼ 4.8 Hz, 1H),
7.56 (d, 3J ¼ 4.8 Hz,1H), 8.28 (d, 3J ¼ 4.8 Hz,1H), 8.54 (s,1H); 13C{1H}
NMR (CDCl3)
d 22.95, 27.62, 50.45, 116.44, 120.04, 124.04, 126.26,
126.72, 129.29, 129.73, 130.62, 143.03, 143.28, 145.07; HRMScalc
:
211.1235 for C14H15N2 [M þ H]þ; HRMSmeas: 211.1228.
4.2.2.11. N-(2-pyridyl)-3-ethyl-aniline (Table 5, entry 6). 1H NMR
(CDCl3)
d
1.25 (t, 3J ¼ 7.6 Hz, 3H), 2.65 (q, 3J ¼ 7.6 Hz, 2H), 6.51 (s,
1H), 6.73 (dd, 3J ¼ 7.2 Hz, 3J ¼ 4.8 Hz, 1H), 6.88 (d, 3J ¼ 8.0 Hz, 1H),
6.90 (d, 3J ¼ 7.2 Hz, 1H), 7.13 (s, 1H), 7.15 (d, 3J ¼ 8.0 Hz, 1H), 7.25 (t,
3J ¼ 8.0 Hz, 1H), 7.49 (td, 3J ¼ 7.2 Hz, 4J ¼ 1.2 Hz, 1H), 8.20 (dd,
3J ¼ 4.8 Hz, 4J ¼ 1.2 Hz, 1H); 13C{1H} NMR (CDCl3)
d 15.71, 29.02,
108.20, 115.07, 117.89, 120.13, 122.71, 129.32, 137.81, 140.44, 145.76,
148.58, 156.14; HRMScalc
HRMSmeas: 199.1232.
:
199.1235 for C13H15N2 [M
þ
H]þ;
[44] B.P. Fors, N.R. Davis, S.L. Buchwald, J. Am. Chem. Soc. 131 (2009) 5766e5768.
[45] R.J. Lundgren, A. Sappong-Kumankumah, M. Stradiotto, Chem. Eur. J. 16
(2010) 1983e1991.
Acknowledgments
[46] G. Marzaro, A. Guiotto, A. Chilin, Green Chem. 11 (2009) 774e776.
[47] T.J. Barker, E.R. Jarvo, Angew. Chem. Int. Ed. 50 (2011) 8325e8328.
[48] T. Kubo, C. Katoh, K. Yamada, K. Okano, H. Tokuyama, T. Fukuyama, Tetra-
hedron 64 (2008) 11230e11236.
[49] V. Khedkar, A. Tillack, M. Beller, Org. Lett. 5 (2003) 4767e4770.
[50] L. Ou, J. Shao, G. Zhang, Y. Yu, Tetrahedron Lett. 52 (2011) 1430e1431.
[51] S.R. Stauffer, M.A. Steinbeiser, Tetrahedron Lett. 46 (2005) 2571e2575.
[52] Q. Shen, T. Ogata, J.F. Hartwig, J. Am. Chem. Soc. 130 (2008) 6586e6596.
[53] L. Shi, M. Wang, C.-A. Fan, F.-M. Zhang, Y.-Q. Tu, Org. Lett. 5 (2003) 3515e
3517.
[54] A. Ehrentraut, A. Zapf, M. Beller, J. Mol. Catal. A Chem. 182 (2002) 515e523.
[55] T.J. Barker, E.R. Jarvo, J. Am. Chem. Soc. 131 (2009) 15598e15599.
[56] W.H. Pearson, W.K. Fang, J. Org. Chem. 60 (1995) 4960e4961.
[57] J.P. Wolfe, H. Tomori, J.P. Sadighi, J.J. Yin, S.L. Buchwald, J. Org. Chem. 65 (2000)
1158e1174.
This material is based upon work supported by the National
Science Foundation under CHE-0841611. D.S. acknowledges
support through the First Year Summer Research Experience
program (funding Summer 2010), Undergraduate Summer
Research and Creative Activity Program (funding Summers 2011
and 2012), and the Charles A. Sullivan Honors Fellowship Award
program (funding Summers 2011 and 2012) administered by the
University of Toledo Office of Undergraduate Research. We would
also like to acknowledge Dr. Andrew R. Shaffer, Dr. Glenn Kuchen-
beiser, Dr. John F. Beck, Ksenia Kriatchkova, and Aaron Jones for
early contributions to this project.
[58] Y.-H. Lee, Y.-C. Chen, J.-C. Hsieh, Eur. J. Org. Chem. 2012 (2012) 247e250.
[59] C. Desmarets, R. Schneider, Y. Fort, J. Org. Chem. 67 (2002) 3029e3036.
[60] H.C. Rudbeck, I. Johannsen, O. Nielsen, T. Ruhland, M.B. Sommer, D. Tanner,
R. Dancer, Synthesis 2005 (2005) 3456e3462.
[61] Q. Dai, W.Z. Gao, D. Liu, L.M. Kapes, X.M. Zhang, J. Org. Chem. 71 (2006) 3928e
3934.
[62] R. Omar-Amrani, R. Schneider, Y. Fort, Synthesis (2004) 2527e2534.
[63] B.J. Jung, J.I. Lee, H.Y. Chu, L.M. Do, J. Lee, H.K. Shim, J. Mater. Chem. 15 (2005)
2470e2475.
[64] J. Meneyrol, P. Helissey, C. Tratrat, S. Giorgi-Renault, H.P. Husson, Synth.
Commun. 31 (2001) 987e992.
[65] Z.P. Li, C.J. Li, J. Am. Chem. Soc. 127 (2005) 6968e6969.
[66] M.J. Cawley, F.G.N. Cloke, R.J. Fitzmaurice, S.E. Pearson, J.S. Scott, S. Caddick,
Org. Biomol. Chem. 6 (2008) 2820e2825.
[67] K. Matsubara, K. Ueno, Y. Koga, K. Hara, J. Org. Chem. 72 (2007) 5069e5076.
[68] A. Komaromi, Z. Novak, Adv. Synth. Catal. 352 (2010) 1523e1532.
[69] M.E. Buden, V.A. Vaillard, S.E. Martin, R.A. Rossi, J. Org. Chem. 74 (2009) 4490e4498.
[70] H. Yang, Z.-B. Li, D.-S. Shin, L.-Y. Wang, J.-Z. Zhou, H.-B. Qiao, X. Tian, X.-Y. Ma,
H. Zuo, Synlett (2010) 483e487.
Appendix A. Supplementary material
Supplementary data related to this article can be found at http://
References
[1] J. Magano, J.R. Dunetz, Chem. Rev. 111 (2011) 2177e2250.
[2] C.A. Busacca, D.R. Fandrick, J.J. Song, C.H. Senanayake, Adv. Synth. Catal. 353
(2011) 1825e1864.
[3] C. Torborg, M. Beller, Adv. Synth. Catal. 351 (2009) 3027e3043.
[4] Y. Chauvin, Angew. Chem. Int. Ed. 45 (2006) 3740e3747.
[5] R.H. Grubbs, Angew. Chem. Int. Ed. 45 (2006) 3760e3765.
[6] R.R. Schrock, Angew. Chem. Int. Ed. 45 (2006) 3748e3759.
[7] E.-i. Negishi, Angew. Chem. Int. Ed. 50 (2011) 6738e6764.
[8] A. Suzuki, Angew. Chem. Int. Ed. 50 (2011) 6722e6737.