6156
T. Chen et al. / Tetrahedron 68 (2012) 6152e6157
J¼7.0 Hz, 36H), 1.35 (s, 18H); 13C{1H} NMR (100 MHz, CDCl3): 164.7
(t, J¼8.9 Hz), 128.4 (t, J¼19.6 Hz), 126.0 (t, J¼4.9 Hz), 123.7, 39.3 (t,
J¼7.3 Hz), 34.2, 30.3, 28.3 (t, J¼2.5 Hz); 31P{1H} NMR (162 MHz,
CDCl3): 186.4; HRMS (ESI): calcd for C32H58NNiO2P2 m/z 608.32963
(MꢂClꢂþCH3CN)þ, found 608.32938.
705; 1H NMR (500 MHz, CDCl3): 7.17e7.12 (m, 8H), 2.92 (s, 4H); 13
C
{1H} NMR (125 MHz, CDCl3): 147.5, 139.9, 129.7, 121.1, 120.5 (q,
J¼255 Hz), 37.0; 19F{1H} NMR (376 MHz, CDCl3): ꢂ58.2; HRMS
(ESI): calcd for C35H30NNiO4P2 m/z 648.10035 (MꢂClꢂþCH3CN)þ,
found 648.10089.
4.5.9. Complex 2c. Yellow solid (Rf¼0.4, 25% EtOAc/hexanes); 73%
yield; mp 233e235 ꢀC; FTIR (KBr, cmꢂ1): 3050, 2965, 1480, 1411,
1217, 1103, 1013, 975, 737, 689, 567; 1H NMR (600 MHz, CDCl3):
8.02e8.01 (m, 8H), 7.50e7.44 (m, 12H), 7.09 (s, 1H),1.39 (s, 18H); 13C
{1H} NMR (150 MHz, CDCl3): 162.5 (t, J¼10.8 Hz), 133.1 (t,
J¼24.4 Hz), 131.9 (t, J¼6.8 Hz), 131.5, 129.8 (t, J¼22.5 Hz), 128.6 (t,
J¼3.1 Hz), 128.2 (t, J¼3.1 Hz), 125.2, 34.5, 30.2; 31P{1H} NMR
(242 MHz, CDCl3): 141.4; HRMS (ESI): calcd for C40H42NNiO2P2 m/z
688.20443 (MꢂClꢂþCH3CN)þ, found 688.20409.
4.5.19. Compound 3h.29 White solid; 74% yield; 1H NMR (500 MHz,
CDCl3): 6.89 (s, 4H), 2.79 (s, 4H), 2.39 (s, 12H), 2.29 (s, 6H); 13C{1H}
NMR (125 MHz, CDCl3): 136.3, 135.7, 135.2, 129.1, 28.9, 20.8, 20.1.
4.5.20. Compound 3i.30 White solid; 70% yield; 1H NMR (500 MHz,
CDCl3): 7.34e7.31 (m, 2H), 7.27e7.21 (m, 3H), 7.19e7.16 (m, 2H),
7.12e7.09 (m, 1H), 7.03e7.01 (m, 2H), 2.97e2.94 (m, 1H), 2.82e2.80
(m, 1H), 1.29 (d, J¼6.6 Hz, 3H), 1.03 (d, J¼6.6 Hz, 3H); 13C{1H} NMR
(125 MHz, CDCl3): 146.5, 145.8, 128.3, 127.8, 127.8, 127.6, 126.0,
125.7, 47.2, 46.4, 21.0, 17.9.
4.5.10. Complex 2d. Yellow solid (Rf¼0.5, 25% EtOAc/hexanes); 71%
yield; mp 254e256 ꢀC; FTIR (KBr, cmꢂ1): 3051, 2966, 1480, 1434,
1218, 1101, 1014, 873, 737, 689, 566; 1H NMR (400 MHz, CDCl3):
8.02e7.97 (m, 8H), 7.51e7.43 (m, 12H), 7.10 (s, 1H), 1.37 (s, 18H); 13C
{1H} NMR (125 MHz, CDCl3): 162.4 (t, J¼10.9 Hz), 133.0 (t,
J¼25.0 Hz), 132.9 (t, J¼25.0 Hz), 132.3 (t, J¼6.9 Hz), 131.5, 128.5 (t,
J¼5.1 Hz), 128.1 (t, J¼5.7 Hz), 125.2, 34.5, 30.2; 31P{1H} NMR
(162 MHz, CDCl3): 145.3; HRMS (ESI): calcd for C40H42NNiO2P2 m/z
688.20443 (MꢂBrꢂþCH3CN)þ, found 688.20413.
Acknowledgements
We are grateful for the generous financial support from King
Abdullah University of Science and Technology.
Supplementary data
Supplementary data associated with this article can be found in
clude MOL files and InChiKeys of the most important compounds
described in this article.
4.5.11. Complex 2e. Yellow solid (Rf¼0.6, 25% EtOAc/hexanes); 76%
yield; mp 274e276 ꢀC; FTIR (KBr, cmꢂ1): 2991, 2951, 1481, 1435,
1218, 1104, 1013, 876, 852, 743, 690, 567; 1H NMR (600 MHz,
CDCl3): 8.03e8.02 (m, 8H), 7.50e7.45 (m, 12H), 7.18 (s, 1H), 1.41 (s,
18H); 13C{1H} NMR (150 MHz, CDCl3): 162.2 (t, J¼10.4 Hz), 138.6 (t,
J¼19.0 Hz), 133.2 (t, J¼26.1 Hz), 132.9 (t, J¼6.4 Hz), 131.6, 128.4 (t,
J¼4.5 Hz), 128.1 (t, J¼5.8 Hz), 125.2, 34.7, 30.3; 31P{1H} NMR
(242 MHz, CDCl3): 152.7; HRMS (ESI): calcd for C40H42NNiO2P2 m/z
688.20443 (MꢂIꢂþCH3CN)þ, found 688.20479.
References and notes
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4.5.12. Compound 3a.20e White solid; 90% yield; 1H NMR
(500 MHz, CDCl3): 7.30e7.27 (m, 4H), 7.21e7.18 (m, 6H), 2.92 (s,
4H); 13C{1H} NMR (125 MHz, CDCl3): 141.8, 128.4, 128.3, 125.9, 37.9.
Niu, J.-L.; Hao, X.-Q.; Gong, J.-F.; Song, M.-P. Dalton Trans. 2011, 40, 5135e5150;
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4.5.13. Compound 3b.25 White solid; 82% yield; 1H NMR (500 MHz,
CDCl3): 7.09e7.06 (m, 4H), 6.97e6.93 (m, 4H), 2.86 (s, 4H); 13C{1H}
NMR (125 MHz, CDCl3): 161.3 (d, J¼243.5 Hz), 136.9 (d, J¼3.16 Hz),
128.3, 125.9, 37.9; 19F{1H} NMR (376 MHz, CDCl3): ꢂ117.7.
4. (a) Huang, K.-W.; Han, J. H.; Musgrave, C. B.; Fujita, E. Organometallics 2006, 26,
508e513; (b) Huang, K.-W.; Grills, D. C.; Han, J. H.; Szalda, D. J.; Fujita, E. Inorg.
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4.5.14. Compound 3c.20e White solid; 92% yield; 1H NMR (500 MHz,
CDCl3): 7.15 (s, 8H), 2.91 (s, 4H), 2.38 (s, 6H); 13C{1H} NMR
(125 MHz, CDCl3): 138.8, 135.3, 129.0, 128.3, 37.6, 21.0.
€
5. (a) Gottker-Schnetmann, I.; Brookhart, M. J. Am. Chem. Soc. 2004, 126,
4.5.15. Compound 3d.26 Colorless oil; 91% yield; 1H NMR (500 MHz,
CDCl3): 7.24e7.21 (m, 2H), 7.07e7.04 (m, 6H), 2.90 (s, 4H), 2.37 (s,
6H); 13C{1H} NMR (125 MHz, CDCl3): 141.9, 137.9, 129.2, 128.2,
126.6, 125.4, 38.0, 21.4.
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4.5.16. Compound 3e.27 White solid; 93% yield; 1H NMR (500 MHz,
CDCl3): 7.35e7.33 (m, 4H), 7.20e7.18 (m, 4H), 2.89 (s, 4H), 1.33 (s,
18H); 13C{1H} NMR (125 MHz, CDCl3): 148.7, 139.0, 128.0, 125.2,
37.4, 34.4, 31.4.
8. (a) Gao, R.; Zhang, M.; Liang, T.; Wang, F.; Sun, W.-H. Organometallics 2008, 27,
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4.5.17. Compound 3f.28 White solid; 43% yield; 1H NMR (500 MHz,
CDCl3): 7.54 (d, J¼8.0 Hz, 4H), 7.25 (d, J¼8.0 Hz, 4H), 2.99 (s, 4H); 13
C
{1H} NMR (125 MHz, CDCl3): 145.0, 128.7, 128.5 (q, J¼32.4 Hz),
ꢁ
ꢁ
9. (a) Campora, J.; Palma, P.; del Río, D.; Alvarez, E. Organometallics 2004, 23,
125.3 (q, J¼3.5 Hz), 37.2; 19F{1H} NMR (376 MHz, CDCl3): ꢂ62.6.
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4.5.18. Compound 3g. Colorless oil (Rf¼0.8, 12% EtOAc/hexanes);
81% yield; FTIR (CH2Cl2, cmꢂ1): 3053, 2930, 1508, 1257, 1164, 735,