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the resulting mixture was stirred at room temperature for 24 h.
After that time the precipitate was collected and washed three
times with THF to afford the desired solid product in sufficient
purity (130 mg, quant).
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1H NMR (400 MHz, CDCl3) δ 8.83 (dd, J8,10 = 2.1 Hz, J7,10 =
0.9 Hz, 2H, H-10), 8.70 (ddd, J1,2 = 4.8 Hz, J1,3 = 1.8 Hz, J1,4 =
0.9 Hz, 2H, H-1), 8.48–8.40 (m, 4H, H-4, H-7), 7.95 (dd, J7,8 =
8.3 Hz, J8,10 = 2.1 Hz, 2H, H-8), 7.84 (ddd, J1,3 = 1.8 Hz, J2,3 =
7.6 Hz, J3,4 = 7.8 Hz, 2H, H-3), 7.80 (dd, J14,16 = 1.6 Hz, J15,16
= 0.8 Hz, 1H, H-16), 7.57 (dd, J14,15 = 7.7 Hz, J14,16 = 1.6 Hz,
2H, H-14), 7.40 (dd, J14,15 = 7.7 Hz, J15,16 = 0.8 Hz, 2H, H-15),
7.33 (ddd, J1,2 = 4.8 Hz, J2,3 = 7.6 Hz, J2,4 = 1.2 Hz, 2H, H-2)
ppm; 13C NMR (100 MHz, CDCl3) δ 155.1 (C-6), 154.3 (C-5),
151.9 (C-10), 148.9 (C-1), 139.7 (C-8), 137.8 (C-3), 135.0
(C-16), 132.1 (C-14), 128.9 (C-15), 124.3 (C-2), 123.3 (C-7),
121.8 (C-4), 120.8 (C-13), 120.4 (C-9), 92.8(C-11), 87.3
(C-12); ESIMS (pos.) m/z: 457.1 [M + Na]+, 435.2 [M + H]+;
HRMS–ESI (m/z): [M + Na]+ calcd for C30H18N4Na, 457.1424;
found, 457.1420; Anal. calcd for C30H18N4·H2O: C, 79.36; H,
4.46; N, 12.38; found: C, 79.87; H, 4.95; N, 12.48 (%).
10.Zhao, L.; Northrop, B. H.; Zheng, Y.-R.; Yang, H.-B.; Lee, H. J.;
Lee, Y. M.; Park, J. Y.; Chi, K.-W.; Stang, P. J. J. Org. Chem. 2008, 73,
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17.Weilandt, T.; Kiehne, U.; Schnakenburg, G.; Lützen, A.
18.Dalla Favera, N.; Kiehne, U.; Bunzen, J.; Hytteballe, S.; Lützen, A.;
Piguet, C. Angew. Chem. 2010, 122, 129–132.
Preparation and characterization of the metal complexes:
[Cu(H3CCN)4]BF4 (6.3 mg, 20 µmol) were dissolved in
DMSO-d6 (1 mL). This solution (500 µL) were added to (rac)-1
(4.26 mg, 10 µmol) and the remaining 500 µL of the solution
were added to 2 (4.34 mg, 10 µmol), respectively. The resulting
solutions were characterized by NMR. For the ESIMS studies
small aliquots of these solutions (10 µL) were taken and diluted
with acetone (1 mL). Subsequently the DMSO solutions were
mixed and again characterized by NMR. For the ESIMS study a
small aliquot of the mixed solution (10 µL) was taken and
diluted with acetone (1 mL).
Angew. Chem., Int. Ed. 2010, 49, 125–128.
19.Weilandt, T.; Kiehne, U.; Bunzen, J.; Schnakenburg, G.; Lützen, A.
20.Gütz, C.; Hovorka, R.; Schnakenburg, G.; Lützen, A. Chem. – Eur. J.
21.Gütz, C.; Hovorka, R.; Stobe, C.; Struch, N.; Topić, F.;
Schnakenburg, G.; Rissanen, K.; Lützen, A. Eur. J. Org. Chem. 2014,
22.Hovorka, R.; Hytteballe, S.; Piehler, T.; Meyer-Eppler, G.; Topić, F.;
Rissanen, K.; Engeser, M.; Lützen, A. Beilstein J. Org. Chem. 2014,
Acknowledgements
We are grateful to the DFG for financial support.
23.Meyer-Eppler, G.; Topić, F.; Schnakenburg, G.; Rissanen, K.;
Lützen, A. Eur. J. Inorg. Chem. 2014, 2495–2501.
24.Krämer, R.; Lehn, J.-M.; Marquis-Rigault, A.
Proc. Natl. Acad. Sci. U. S. A. 1993, 90, 5394–5398.
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